# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12a
_database_code_depnum_ccdc_archive 'CCDC 1436752'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT129_12a                 
;
PROBLEM: Unusual Space group Specified ..................       I1A1 Check 
RESPONSE: reported space group correct.
;
# end Validation Reply Form
_audit_creation_date             2014-11-10
_audit_creation_method           'by CrystalStructure 4.1'

_chemical_formula_sum            'C15 H18 F4 O'
_chemical_formula_moiety         'C15 H18 F4 O'
_chemical_formula_weight         290.30
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
_space_group_IT_number           9
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,-Y,+Z
3 1/2+X,1/2+Y,1/2+Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.562(6)
_cell_length_b                   6.267(2)
_cell_length_c                   19.695(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.75(3)
_cell_angle_gamma                90.0000
_cell_volume                     1419.9(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2748
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608.00
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 11.628
_diffrn_reflns_number            7749
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_theta_max         25.312
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2534
_reflns_number_gt                2418
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0694
_refine_ls_wR_factor_gt          0.0688
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2534
_refine_ls_number_parameters     182
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0422P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.12
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1113 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S., Flack, H.D. and Wagner, T. Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.91186(11) 0.06057(19) 0.82700(8) 0.0452(3) Uani 1 4 d . . .
F3 F 0.84953(11) 0.1789(2) 0.95240(7) 0.0452(3) Uani 1 4 d . . .
F5 F 0.70459(12) 0.5636(2) 0.93818(8) 0.0470(3) Uani 1 4 d . . .
F6 F 0.67693(11) 0.69059(19) 0.80409(8) 0.0480(3) Uani 1 4 d . . .
O8 O 0.88354(13) 0.4846(3) 0.71161(8) 0.0397(4) Uani 1 4 d . . .
C1 C 0.78722(17) 0.3670(3) 0.80858(10) 0.0295(4) Uani 1 4 d . . .
C2 C 0.90381(17) 0.2794(3) 0.84236(11) 0.0314(4) Uani 1 4 d . . .
C3 C 0.92629(18) 0.3084(4) 0.91866(12) 0.0394(5) Uani 1 4 d . . .
C4 C 0.9114(2) 0.5401(4) 0.93884(12) 0.0420(5) Uani 1 4 d . . .
C5 C 0.8007(2) 0.6431(3) 0.90680(12) 0.0392(5) Uani 1 4 d . . .
C6 C 0.78327(18) 0.6025(3) 0.83133(11) 0.0326(4) Uani 1 4 d . . .
C7 C 0.68061(17) 0.2373(4) 0.82594(11) 0.0344(5) Uani 1 4 d . . .
C8 C 0.78864(19) 0.3607(3) 0.73101(11) 0.0364(5) Uani 1 4 d . . .
C9 C 0.8783(2) 0.5153(4) 0.64005(12) 0.0410(5) Uani 1 4 d . . .
C10 C 0.97220(18) 0.6713(3) 0.62484(11) 0.0347(5) Uani 1 4 d . . .
C11 C 0.9839(2) 0.8665(4) 0.65867(12) 0.0427(5) Uani 1 4 d . . .
C12 C 1.0687(3) 1.0116(4) 0.64293(14) 0.0510(6) Uani 1 4 d . . .
C13 C 1.1411(2) 0.9628(4) 0.59364(14) 0.0513(7) Uani 1 4 d . . .
C14 C 1.13051(19) 0.7695(4) 0.56004(12) 0.0466(6) Uani 1 4 d . . .
C15 C 1.0468(2) 0.6231(4) 0.57592(11) 0.0390(5) Uani 1 4 d . . .
H2 H 0.96747 0.35444 0.82108 0.0377 Uiso 1 4 calc R . .
H3 H 1.00794 0.26357 0.93347 0.0473 Uiso 1 4 calc R . .
H4A H 0.91252 0.5482 0.9891 0.0504 Uiso 1 4 calc R . .
H4B H 0.97863 0.62287 0.9257 0.0504 Uiso 1 4 calc R . .
H5 H 0.80612 0.8006 0.91462 0.0470 Uiso 1 4 calc R . .
H6 H 0.84636 0.67971 0.81022 0.0391 Uiso 1 4 calc R . .
H7A H 0.67735 0.23688 0.87547 0.0412 Uiso 1 4 calc R . .
H7B H 0.68713 0.0904 0.80973 0.0412 Uiso 1 4 calc R . .
H7C H 0.60963 0.30241 0.80364 0.0412 Uiso 1 4 calc R . .
H8A H 0.79646 0.21134 0.71578 0.0437 Uiso 1 4 calc R . .
H8B H 0.71459 0.41835 0.70878 0.0437 Uiso 1 4 calc R . .
H9A H 0.80105 0.57197 0.62264 0.0492 Uiso 1 4 calc R . .
H9B H 0.88995 0.3775 0.61714 0.0492 Uiso 1 4 calc R . .
H11 H 0.934 0.90087 0.69257 0.0512 Uiso 1 4 calc R . .
H12 H 1.0766 1.14427 0.66625 0.0612 Uiso 1 4 calc R . .
H13 H 1.19836 1.06245 0.58277 0.0615 Uiso 1 4 calc R . .
H14 H 1.18043 0.73634 0.52603 0.0559 Uiso 1 4 calc R . .
H15 H 1.04055 0.48938 0.55314 0.0468 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F2 C2 1.410(2) yes . .
F3 C3 1.416(3) yes . .
F5 C5 1.415(3) yes . .
F6 C6 1.404(2) yes . .
O8 C8 1.427(3) yes . .
O8 C9 1.418(3) yes . .
C1 C2 1.543(3) yes . .
C1 C6 1.544(3) yes . .
C1 C7 1.543(3) yes . .
C1 C8 1.530(3) yes . .
C2 C3 1.510(3) yes . .
C3 C4 1.520(3) yes . .
C4 C5 1.514(3) yes . .
C5 C6 1.502(3) yes . .
C9 C10 1.513(3) yes . .
C10 C11 1.393(3) yes . .
C10 C15 1.389(3) yes . .
C11 C12 1.395(4) yes . .
C12 C13 1.378(4) yes . .
C13 C14 1.380(4) yes . .
C14 C15 1.392(4) yes . .
C2 H2 1.000 no . .
C3 H3 1.000 no . .
C4 H4A 0.990 no . .
C4 H4B 0.990 no . .
C5 H5 1.000 no . .
C6 H6 1.000 no . .
C7 H7A 0.980 no . .
C7 H7B 0.980 no . .
C7 H7C 0.980 no . .
C8 H8A 0.990 no . .
C8 H8B 0.990 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C8 O8 C9 112.50(16) yes . . .
C2 C1 C6 105.34(15) yes . . .
C2 C1 C7 113.58(17) yes . . .
C2 C1 C8 108.98(17) yes . . .
C6 C1 C7 113.04(17) yes . . .
C6 C1 C8 108.52(17) yes . . .
C7 C1 C8 107.25(16) yes . . .
F2 C2 C1 109.08(15) yes . . .
F2 C2 C3 108.77(17) yes . . .
C1 C2 C3 116.25(18) yes . . .
F3 C3 C2 110.16(17) yes . . .
F3 C3 C4 109.40(18) yes . . .
C2 C3 C4 111.23(18) yes . . .
C3 C4 C5 114.30(18) yes . . .
F5 C5 C4 109.63(18) yes . . .
F5 C5 C6 109.81(17) yes . . .
C4 C5 C6 111.38(19) yes . . .
F6 C6 C1 108.37(15) yes . . .
F6 C6 C5 109.71(18) yes . . .
C1 C6 C5 116.37(17) yes . . .
O8 C8 C1 109.81(17) yes . . .
O8 C9 C10 108.95(18) yes . . .
C9 C10 C11 120.7(2) yes . . .
C9 C10 C15 120.3(2) yes . . .
C11 C10 C15 119.0(2) yes . . .
C10 C11 C12 120.2(2) yes . . .
C11 C12 C13 120.1(2) yes . . .
C12 C13 C14 120.1(2) yes . . .
C13 C14 C15 120.1(2) yes . . .
C10 C15 C14 120.4(2) yes . . .
F2 C2 H2 107.467 no . . .
C1 C2 H2 107.465 no . . .
C3 C2 H2 107.464 no . . .
F3 C3 H3 108.660 no . . .
C2 C3 H3 108.663 no . . .
C4 C3 H3 108.667 no . . .
C3 C4 H4A 108.679 no . . .
C3 C4 H4B 108.678 no . . .
C5 C4 H4A 108.688 no . . .
C5 C4 H4B 108.684 no . . .
H4A C4 H4B 107.612 no . . .
F5 C5 H5 108.651 no . . .
C4 C5 H5 108.649 no . . .
C6 C5 H5 108.658 no . . .
F6 C6 H6 107.336 no . . .
C1 C6 H6 107.336 no . . .
C5 C6 H6 107.344 no . . .
C1 C7 H7A 109.470 no . . .
C1 C7 H7B 109.472 no . . .
C1 C7 H7C 109.470 no . . .
H7A C7 H7B 109.474 no . . .
H7A C7 H7C 109.474 no . . .
H7B C7 H7C 109.467 no . . .
O8 C8 H8A 109.710 no . . .
O8 C8 H8B 109.713 no . . .
C1 C8 H8A 109.703 no . . .
C1 C8 H8B 109.696 no . . .
H8A C8 H8B 108.187 no . . .
O8 C9 H9A 109.892 no . . .
O8 C9 H9B 109.890 no . . .
C10 C9 H9A 109.901 no . . .
C10 C9 H9B 109.900 no . . .
H9A C9 H9B 108.304 no . . .
C10 C11 H11 119.899 no . . .
C12 C11 H11 119.894 no . . .
C11 C12 H12 119.928 no . . .
C13 C12 H12 119.928 no . . .
C12 C13 H13 119.954 no . . .
C14 C13 H13 119.946 no . . .
C13 C14 H14 119.964 no . . .
C15 C14 H14 119.963 no . . .
C10 C15 H15 119.770 no . . .
C14 C15 H15 119.781 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C8 O8 C9 C10 172.55(15) no . . . .
C9 O8 C8 C1 -169.93(15) no . . . .
C2 C1 C6 F6 -178.04(15) no . . . .
C2 C1 C6 C5 -53.9(2) no . . . .
C6 C1 C2 F2 176.99(15) no . . . .
C6 C1 C2 C3 53.6(2) no . . . .
C7 C1 C2 F2 52.8(2) no . . . .
C7 C1 C2 C3 -70.6(2) no . . . .
C2 C1 C8 O8 -58.6(2) no . . . .
C8 C1 C2 F2 -66.7(2) no . . . .
C8 C1 C2 C3 169.88(14) no . . . .
C7 C1 C6 F6 -53.5(2) no . . . .
C7 C1 C6 C5 70.7(2) no . . . .
C6 C1 C8 O8 55.6(2) no . . . .
C8 C1 C6 F6 65.4(2) no . . . .
C8 C1 C6 C5 -170.48(15) no . . . .
C7 C1 C8 O8 178.03(15) no . . . .
F2 C2 C3 F3 -55.0(2) no . . . .
F2 C2 C3 C4 -176.49(13) no . . . .
C1 C2 C3 F3 68.5(2) no . . . .
C1 C2 C3 C4 -52.9(2) no . . . .
F3 C3 C4 C5 -73.8(2) no . . . .
C2 C3 C4 C5 48.1(2) no . . . .
C3 C4 C5 F5 73.3(2) no . . . .
C3 C4 C5 C6 -48.4(2) no . . . .
F5 C5 C6 F6 55.3(2) no . . . .
F5 C5 C6 C1 -68.2(2) no . . . .
C4 C5 C6 F6 176.89(16) no . . . .
C4 C5 C6 C1 53.4(2) no . . . .
O8 C9 C10 C11 -50.8(2) no . . . .
O8 C9 C10 C15 130.35(18) no . . . .
C9 C10 C11 C12 -178.23(17) no . . . .
C9 C10 C15 C14 177.66(17) no . . . .
C11 C10 C15 C14 -1.2(3) no . . . .
C15 C10 C11 C12 0.6(3) no . . . .
C10 C11 C12 C13 0.2(3) no . . . .
C11 C12 C13 C14 -0.5(4) no . . . .
C12 C13 C14 C15 -0.1(4) no . . . .
C13 C14 C15 C10 0.9(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F2 F3 2.743(2) no . .
F2 O8 3.491(2) no . .
F2 C7 2.892(3) no . .
F2 C8 2.933(3) no . .
F3 F5 2.933(2) no . .
F3 C1 3.086(3) no . .
F3 C5 3.080(3) no . .
F3 C6 3.599(3) no . .
F3 C7 3.030(3) no . .
F5 F6 2.746(3) no . .
F5 C1 3.072(3) no . .
F5 C2 3.593(3) no . .
F5 C3 3.078(3) no . .
F5 C7 3.003(3) no . .
F6 O8 3.400(2) no . .
F6 C7 2.873(3) no . .
F6 C8 2.896(3) no . .
O8 C2 2.867(3) no . .
O8 C6 2.828(3) no . .
O8 C11 2.899(3) no . .
O8 C15 3.531(3) no . .
C1 C4 3.014(3) no . .
C2 C5 2.920(3) no . .
C3 C6 2.919(3) no . .
C3 C7 3.250(3) no . .
C5 C7 3.239(3) no . .
C10 C13 2.787(4) no . .
C11 C14 2.770(4) no . .
C12 C15 2.769(4) no . .
F2 F6 3.565(2) no . 1_545
F2 F6 3.508(2) no . 2_565
F2 C5 3.372(3) no . 1_545
F2 C6 3.238(3) no . 1_545
F3 C5 3.507(3) no . 1_545
F3 C14 3.508(3) no . 3_445
F5 C3 3.301(3) no . 2_465
F5 C4 3.452(3) no . 2_465
F5 C13 3.281(4) no . 3_445
F5 C14 3.210(3) no . 3_445
F6 F2 3.565(2) no . 1_565
F6 F2 3.508(2) no . 2_465
F6 C2 3.324(3) no . 2_465
F6 C7 3.453(3) no . 1_565
C2 F6 3.324(3) no . 2_565
C3 F5 3.301(3) no . 2_565
C4 F5 3.452(3) no . 2_565
C4 C14 3.511(3) no . 4_565
C5 F2 3.372(3) no . 1_565
C5 F3 3.507(3) no . 1_565
C6 F2 3.238(3) no . 1_565
C7 F6 3.453(3) no . 1_545
C13 F5 3.281(4) no . 3_554
C14 F3 3.508(3) no . 3_554
C14 F5 3.210(3) no . 3_554
C14 C4 3.511(3) no . 4_564
F2 H3 2.6045 no . .
F2 H7A 3.1626 no . .
F2 H7B 2.5933 no . .
F2 H8A 2.6241 no . .
F3 H2 3.2350 no . .
F3 H4A 2.5109 no . .
F3 H4B 3.2255 no . .
F3 H7A 2.4056 no . .
F3 H7B 3.2668 no . .
F5 H4A 2.5124 no . .
F5 H4B 3.2239 no . .
F5 H6 3.2241 no . .
F5 H7A 2.3956 no . .
F5 H7C 3.2130 no . .
F6 H5 2.6066 no . .
F6 H7A 3.1717 no . .
F6 H7C 2.5539 no . .
F6 H8B 2.6053 no . .
O8 H2 2.4159 no . .
O8 H6 2.3705 no . .
O8 H11 2.7076 no . .
C1 H3 3.4243 no . .
C1 H4B 3.4305 no . .
C1 H5 3.4210 no . .
C2 H4A 3.3378 no . .
C2 H4B 2.7911 no . .
C2 H6 2.6552 no . .
C2 H7A 2.7738 no . .
C2 H7B 2.7876 no . .
C2 H7C 3.4135 no . .
C2 H8A 2.7052 no . .
C2 H8B 3.3635 no . .
C3 H5 3.3810 no . .
C3 H6 3.2305 no . .
C3 H7A 2.9527 no . .
C3 H7B 3.5954 no . .
C4 H2 2.7300 no . .
C4 H6 2.7143 no . .
C4 H7A 3.4375 no . .
C5 H2 3.2390 no . .
C5 H3 3.3794 no . .
C5 H7A 2.9530 no . .
C5 H7C 3.5594 no . .
C6 H2 2.6606 no . .
C6 H4A 3.3278 no . .
C6 H4B 2.7807 no . .
C6 H7A 2.7781 no . .
C6 H7B 3.4089 no . .
C6 H7C 2.7649 no . .
C6 H8A 3.3586 no . .
C6 H8B 2.7210 no . .
C7 H2 3.4076 no . .
C7 H6 3.4019 no . .
C7 H8A 2.6664 no . .
C7 H8B 2.6357 no . .
C8 H2 2.5863 no . .
C8 H6 2.5820 no . .
C8 H7A 3.3296 no . .
C8 H7B 2.6487 no . .
C8 H7C 2.6564 no . .
C8 H9A 2.5278 no . .
C8 H9B 2.6341 no . .
C9 H6 3.5606 no . .
C9 H8A 2.6519 no . .
C9 H8B 2.5096 no . .
C9 H11 2.6812 no . .
C9 H15 2.6680 no . .
C10 H12 3.2730 no . .
C10 H14 3.2693 no . .
C11 H9A 2.8426 no . .
C11 H9B 3.3260 no . .
C11 H13 3.2607 no . .
C11 H15 3.2567 no . .
C12 H14 3.2465 no . .
C13 H11 3.2580 no . .
C13 H15 3.2566 no . .
C14 H12 3.2466 no . .
C15 H9A 3.0892 no . .
C15 H9B 2.5710 no . .
C15 H11 3.2568 no . .
C15 H13 3.2594 no . .
H2 H3 2.2881 no . .
H2 H4B 2.6531 no . .
H2 H6 2.4702 no . .
H2 H8A 2.8625 no . .
H2 H8B 3.5080 no . .
H3 H4A 2.4169 no . .
H3 H4B 2.2800 no . .
H4A H5 2.4095 no . .
H4B H5 2.2758 no . .
H4B H6 2.6348 no . .
H5 H6 2.2825 no . .
H6 H8A 3.4919 no . .
H6 H8B 2.8959 no . .
H6 H11 2.9643 no . .
H7A H8A 3.5611 no . .
H7A H8B 3.5411 no . .
H7B H8A 2.4626 no . .
H7B H8B 2.8990 no . .
H7C H8A 2.9554 no . .
H7C H8B 2.4382 no . .
H8A H9A 2.9147 no . .
H8A H9B 2.5392 no . .
H8B H9A 2.2680 no . .
H8B H9B 2.8577 no . .
H9A H11 2.8433 no . .
H9A H15 3.2509 no . .
H9B H15 2.3562 no . .
H11 H12 2.3420 no . .
H12 H13 2.3263 no . .
H13 H14 2.3286 no . .
H14 H15 2.3386 no . .
F2 H4B 3.4057 no . 1_545
F2 H5 2.7476 no . 1_545
F2 H6 2.5159 no . 1_545
F2 H7B 3.3700 no . 2_555
F2 H7C 3.2902 no . 2_555
F2 H11 2.8658 no . 1_545
F3 H5 2.5201 no . 1_545
F3 H9B 3.2507 no . 4_555
F3 H14 2.5735 no . 3_445
F3 H15 3.0081 no . 4_555
F5 H2 3.4399 no . 2_465
F5 H3 2.5118 no . 2_465
F5 H4B 2.8500 no . 2_465
F5 H13 2.8558 no . 3_445
F5 H14 2.7156 no . 3_445
F6 H2 2.4938 no . 2_465
F6 H3 3.3749 no . 2_465
F6 H7B 2.5103 no . 1_565
F6 H12 3.0259 no . 2_475
O8 H7C 3.3094 no . 2_565
O8 H12 3.2754 no . 1_545
C2 H5 3.5537 no . 1_545
C3 H5 3.4700 no . 1_545
C3 H15 3.3973 no . 4_555
C5 H3 3.5262 no . 2_465
C5 H7B 3.5687 no . 1_565
C6 H7B 3.2669 no . 1_565
C7 H2 3.5468 no . 2_465
C7 H4B 3.3166 no . 2_465
C7 H5 3.4843 no . 1_545
C8 H11 3.4581 no . 1_545
C9 H12 3.2701 no . 1_545
C9 H13 3.4832 no . 2_475
C9 H14 3.4258 no . 2_465
C10 H4A 3.2164 no . 4_564
C10 H8B 3.1583 no . 2_565
C10 H12 3.5822 no . 1_545
C11 H4A 3.4013 no . 4_564
C11 H7C 3.2487 no . 2_565
C11 H8A 3.3350 no . 1_565
C11 H8B 3.2781 no . 2_565
C11 H9B 3.4537 no . 1_565
C11 H13 3.5136 no . 2_475
C12 H4A 3.3890 no . 4_564
C12 H7B 3.4892 no . 2_565
C12 H8A 3.1918 no . 2_565
C12 H8B 3.3687 no . 2_565
C12 H9B 3.0950 no . 1_565
C12 H15 3.4764 no . 1_565
C13 H4A 3.1841 no . 4_564
C13 H8A 3.0561 no . 2_565
C13 H8B 3.3445 no . 2_565
C13 H9A 3.4691 no . 2_575
C13 H9B 3.5743 no . 2_565
C13 H15 3.5625 no . 1_565
C14 H4A 2.9840 no . 4_564
C14 H4B 3.0998 no . 4_564
C14 H8A 3.4534 no . 2_565
C14 H8B 3.2161 no . 2_565
C14 H9A 3.0825 no . 2_565
C14 H9B 3.2305 no . 2_565
C15 H4A 3.0073 no . 4_564
C15 H4B 3.3824 no . 4_564
C15 H8B 3.1087 no . 2_565
C15 H9A 3.2318 no . 2_565
C15 H12 3.4882 no . 1_545
H2 F5 3.4399 no . 2_565
H2 F6 2.4938 no . 2_565
H2 C7 3.5468 no . 2_565
H2 H7C 2.7491 no . 2_565
H3 F5 2.5118 no . 2_565
H3 F6 3.3749 no . 2_565
H3 C5 3.5262 no . 2_565
H3 H5 3.5272 no . 2_565
H3 H15 2.8341 no . 4_555
H4A C10 3.2164 no . 4_565
H4A C11 3.4013 no . 4_565
H4A C12 3.3890 no . 4_565
H4A C13 3.1841 no . 4_565
H4A C14 2.9840 no . 4_565
H4A C15 3.0073 no . 4_565
H4A H13 3.2338 no . 3_445
H4A H14 3.4555 no . 3_445
H4A H14 3.3906 no . 4_565
H4A H15 3.4361 no . 4_565
H4B F2 3.4057 no . 1_565
H4B F5 2.8500 no . 2_565
H4B C7 3.3166 no . 2_565
H4B C14 3.0998 no . 4_565
H4B C15 3.3824 no . 4_565
H4B H7A 2.7359 no . 2_565
H4B H7C 3.0036 no . 2_565
H4B H14 3.0338 no . 4_565
H4B H15 3.5153 no . 4_565
H5 F2 2.7476 no . 1_565
H5 F3 2.5201 no . 1_565
H5 C2 3.5537 no . 1_565
H5 C3 3.4700 no . 1_565
H5 C7 3.4843 no . 1_565
H5 H3 3.5272 no . 2_465
H5 H7A 3.1713 no . 1_565
H5 H7B 2.9816 no . 1_565
H6 F2 2.5159 no . 1_565
H6 H7B 3.1639 no . 1_565
H6 H7C 3.0617 no . 2_565
H7A H4B 2.7359 no . 2_465
H7A H5 3.1713 no . 1_545
H7A H14 2.9619 no . 3_445
H7B F2 3.3700 no . 2_455
H7B F6 2.5103 no . 1_545
H7B C5 3.5687 no . 1_545
H7B C6 3.2669 no . 1_545
H7B C12 3.4892 no . 2_465
H7B H5 2.9816 no . 1_545
H7B H6 3.1639 no . 1_545
H7B H11 3.5413 no . 2_465
H7B H12 3.3254 no . 2_465
H7C F2 3.2902 no . 2_455
H7C O8 3.3094 no . 2_465
H7C C11 3.2487 no . 2_465
H7C H2 2.7491 no . 2_465
H7C H4B 3.0036 no . 2_465
H7C H6 3.0617 no . 2_465
H7C H11 3.1052 no . 2_465
H8A C11 3.3350 no . 1_545
H8A C12 3.1918 no . 2_465
H8A C13 3.0561 no . 2_465
H8A C14 3.4534 no . 2_465
H8A H11 2.5825 no . 1_545
H8A H12 3.5003 no . 1_545
H8A H12 3.4473 no . 2_465
H8A H13 3.2401 no . 2_465
H8B C10 3.1583 no . 2_465
H8B C11 3.2781 no . 2_465
H8B C12 3.3687 no . 2_465
H8B C13 3.3445 no . 2_465
H8B C14 3.2161 no . 2_465
H8B C15 3.1087 no . 2_465
H8B H12 3.2393 no . 2_475
H8B H15 3.5419 no . 2_465
H9A C13 3.4691 no . 2_475
H9A C14 3.0825 no . 2_465
H9A C15 3.2318 no . 2_465
H9A H12 3.3288 no . 2_475
H9A H13 2.6625 no . 2_475
H9A H14 2.9610 no . 2_465
H9A H15 3.2043 no . 2_465
H9B F3 3.2507 no . 4_554
H9B C11 3.4537 no . 1_545
H9B C12 3.0950 no . 1_545
H9B C13 3.5743 no . 2_465
H9B C14 3.2305 no . 2_465
H9B H11 3.3522 no . 1_545
H9B H12 2.7039 no . 1_545
H9B H13 3.5591 no . 2_465
H9B H14 2.9541 no . 2_465
H11 F2 2.8658 no . 1_565
H11 C8 3.4581 no . 1_565
H11 H7B 3.5413 no . 2_565
H11 H7C 3.1052 no . 2_565
H11 H8A 2.5825 no . 1_565
H11 H9B 3.3522 no . 1_565
H11 H13 3.3125 no . 2_475
H12 F6 3.0259 no . 2_575
H12 O8 3.2754 no . 1_565
H12 C9 3.2701 no . 1_565
H12 C10 3.5822 no . 1_565
H12 C15 3.4882 no . 1_565
H12 H7B 3.3254 no . 2_565
H12 H8A 3.5003 no . 1_565
H12 H8A 3.4473 no . 2_565
H12 H8B 3.2393 no . 2_575
H12 H9A 3.3288 no . 2_575
H12 H9B 2.7039 no . 1_565
H12 H15 3.1029 no . 1_565
H13 F5 2.8558 no . 3_554
H13 C9 3.4832 no . 2_575
H13 C11 3.5136 no . 2_575
H13 H4A 3.2338 no . 3_554
H13 H8A 3.2401 no . 2_565
H13 H9A 2.6625 no . 2_575
H13 H9B 3.5591 no . 2_565
H13 H11 3.3125 no . 2_575
H13 H15 3.2581 no . 1_565
H14 F3 2.5735 no . 3_554
H14 F5 2.7156 no . 3_554
H14 C9 3.4258 no . 2_565
H14 H4A 3.4555 no . 3_554
H14 H4A 3.3906 no . 4_564
H14 H4B 3.0338 no . 4_564
H14 H7A 2.9619 no . 3_554
H14 H9A 2.9610 no . 2_565
H14 H9B 2.9541 no . 2_565
H15 F3 3.0081 no . 4_554
H15 C3 3.3973 no . 4_554
H15 C12 3.4764 no . 1_545
H15 C13 3.5625 no . 1_545
H15 H3 2.8341 no . 4_554
H15 H4A 3.4361 no . 4_564
H15 H4B 3.5153 no . 4_564
H15 H8B 3.5419 no . 2_565
H15 H9A 3.2043 no . 2_565
H15 H12 3.1029 no . 1_545
H15 H13 3.2581 no . 1_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12b
_database_code_depnum_ccdc_archive 'CCDC 1436753'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2014-12-18
_audit_creation_method           'by CrystalStructure 4.1'

# start Validation Reply Form
_vrf_DIFMX01_12b                 
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*2.00
RESPONSE: Poor crystals but adequate to show configuration difference between 12a and 12b.
;
_vrf_PLAT097_12b                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       2.58 eA-3  
RESPONSE: Poor crystals but adequate to show configuration difference between 12a and 12b.
;


_chemical_formula_sum            'C15 H18 F4 O'
_chemical_formula_moiety         'C15 H18 F4 O'
_chemical_formula_weight         290.30
_chemical_melting_point          ?
_chemical_absolute_configuration syn

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
_space_group_IT_number           29
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,+Y,1/2+Z
3 1/2+X,-Y,+Z
4 -X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   22.574(2)
_cell_length_b                   6.3537(8)
_cell_length_c                   19.1603(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2748.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3194
_cell_measurement_theta_min      24.20
_cell_measurement_theta_max      75.40
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216.00
_exptl_absorpt_coefficient_mu    1.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.948

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            26681
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_theta_max         68.345
_diffrn_reflns_theta_min         3.917
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4955
_reflns_number_gt                4269
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.1577
_refine_ls_wR_factor_ref         0.3507
_refine_ls_wR_factor_gt          0.3205
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4955
_refine_ls_number_parameters     363
_refine_ls_goodness_of_fit_ref   1.547
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         2.58
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F22 F 0.1699(2) 0.4017(7) 0.7485(3) 0.0394(12) Uani 1 1 d . . . . .
F2 F 0.4258(2) 0.1181(8) 0.5896(4) 0.0497(15) Uani 1 1 d . . . . .
F3 F 0.3121(3) 0.0159(8) 0.5659(5) 0.0574(18) Uani 1 1 d . . . . .
F5 F 0.3280(3) 0.6400(11) 0.7022(3) 0.0588(16) Uani 1 1 d . . . . .
F6 F 0.4363(2) 0.4960(8) 0.6702(3) 0.0370(12) Uani 1 1 d . . . . .
F23 F 0.0552(2) 0.4833(8) 0.7745(4) 0.0504(15) Uani 1 1 d . . . . .
F25 F 0.0795(3) -0.1201(11) 0.6287(3) 0.0576(16) Uani 1 1 d . . . . .
F26 F 0.1843(2) 0.0487(8) 0.6641(3) 0.0367(11) Uani 1 1 d . . . . .
O8 O 0.4947(2) 0.3690(10) 0.4711(3) 0.0392(14) Uani 1 1 d . . . . .
O28 O 0.2424(2) 0.1483(9) 0.8636(3) 0.0350(13) Uani 1 1 d . . . . .
C1 C 0.4159(3) 0.4748(11) 0.5466(4) 0.0254(15) Uani 1 1 d . . . . .
C2 C 0.3934(4) 0.2447(12) 0.5439(5) 0.0368(18) Uani 1 1 d . . . . .
H2 H 0.3979 0.1895 0.4953 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3289(4) 0.2300(13) 0.5654(5) 0.0390(19) Uani 1 1 d . . . . .
H3 H 0.3041 0.3073 0.5306 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3184(4) 0.3230(15) 0.6378(5) 0.0397(19) Uani 1 1 d . . . . .
H4A H 0.2759 0.3130 0.6502 0.048 Uiso 1 1 calc R U . . .
H4B H 0.3416 0.2446 0.6731 0.048 Uiso 1 1 calc R U . . .
C5 C 0.3373(4) 0.5479(16) 0.6363(5) 0.0391(19) Uani 1 1 d . . . . .
H5 H 0.3121 0.6238 0.6016 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4017(4) 0.5793(12) 0.6159(4) 0.0337(17) Uani 1 1 d . . . . .
H6 H 0.4099 0.7335 0.6120 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3896(4) 0.5993(14) 0.4867(4) 0.0368(18) Uani 1 1 d . . . . .
H7A H 0.3996 0.7485 0.4922 0.044 Uiso 1 1 calc R U . . .
H7B H 0.3464 0.5826 0.4867 0.044 Uiso 1 1 calc R U . . .
H7C H 0.4057 0.5474 0.4424 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4846(3) 0.4714(13) 0.5375(4) 0.0293(16) Uani 1 1 d . . . . .
H8A H 0.5007 0.6163 0.5371 0.035 Uiso 1 1 calc R U . . .
H8B H 0.5035 0.3917 0.5758 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5555(3) 0.3105(14) 0.4599(4) 0.0342(17) Uani 1 1 d . . . . .
H9A H 0.5723 0.2479 0.5029 0.041 Uiso 1 1 calc R U . . .
H9B H 0.5793 0.4358 0.4473 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5566(3) 0.1541(13) 0.4019(5) 0.0326(17) Uani 1 1 d . . . . .
C11 C 0.5791(3) 0.2015(13) 0.3371(4) 0.0332(16) Uani 1 1 d . . . . .
H11 H 0.5962 0.3354 0.3283 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5762(4) 0.0468(17) 0.2832(5) 0.045(2) Uani 1 1 d . . . . .
H12 H 0.5915 0.0794 0.2383 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5524(4) -0.1450(16) 0.2947(5) 0.045(2) Uani 1 1 d . . . . .
H13 H 0.5509 -0.2460 0.2582 0.054 Uiso 1 1 calc R U . . .
C14 C 0.5297(4) -0.1940(14) 0.3608(6) 0.046(2) Uani 1 1 d . . . . .
H14 H 0.5128 -0.3284 0.3696 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5323(4) -0.0406(14) 0.4147(5) 0.0384(19) Uani 1 1 d . . . . .
H15 H 0.5171 -0.0726 0.4597 0.046 Uiso 1 1 calc R U . . .
C21 C 0.1648(3) 0.0383(12) 0.7867(4) 0.0267(16) Uani 1 1 d . . . . .
C22 C 0.1378(4) 0.2640(12) 0.7924(4) 0.0341(17) Uani 1 1 d . . . . .
H22 H 0.1414 0.3138 0.8418 0.041 Uiso 1 1 calc R U . . .
C23 C 0.0736(3) 0.2709(12) 0.7712(5) 0.0351(18) Uani 1 1 d . . . . .
H23 H 0.0498 0.1866 0.8052 0.042 Uiso 1 1 calc R U . . .
C24 C 0.0634(4) 0.1839(15) 0.6982(5) 0.0405(19) Uani 1 1 d . . . . .
H24A H 0.0206 0.1861 0.6869 0.049 Uiso 1 1 calc R U . . .
H24B H 0.0846 0.2712 0.6634 0.049 Uiso 1 1 calc R U . . .
C25 C 0.0865(4) -0.0402(15) 0.6961(5) 0.0380(19) Uani 1 1 d . . . . .
H25 H 0.0628 -0.1280 0.7293 0.046 Uiso 1 1 calc R U . . .
C26 C 0.1514(3) -0.0566(13) 0.7155(4) 0.0316(16) Uani 1 1 d . . . . .
H26 H 0.1631 -0.2084 0.7159 0.038 Uiso 1 1 calc R U . . .
C27 C 0.1388(4) -0.0986(13) 0.8444(4) 0.0363(18) Uani 1 1 d . . . . .
H27A H 0.1578 -0.2372 0.8436 0.044 Uiso 1 1 calc R U . . .
H27B H 0.0961 -0.1151 0.8369 0.044 Uiso 1 1 calc R U . . .
H27C H 0.1457 -0.0316 0.8897 0.044 Uiso 1 1 calc R U . . .
C28 C 0.2328(3) 0.0552(15) 0.7976(5) 0.0350(17) Uani 1 1 d . . . . .
H28A H 0.2511 -0.0863 0.7960 0.042 Uiso 1 1 calc R U . . .
H28B H 0.2507 0.1429 0.7605 0.042 Uiso 1 1 calc R U . . .
C29 C 0.3031(4) 0.2065(15) 0.8753(5) 0.043(2) Uani 1 1 d . . . . .
H29A H 0.3205 0.2682 0.8325 0.051 Uiso 1 1 calc R U . . .
H29B H 0.3268 0.0821 0.8890 0.051 Uiso 1 1 calc R U . . .
C30 C 0.3019(3) 0.3664(14) 0.9334(4) 0.0335(17) Uani 1 1 d . . . . .
C31 C 0.2807(4) 0.5680(14) 0.9223(5) 0.0373(19) Uani 1 1 d . . . . .
H31 H 0.2676 0.6068 0.8770 0.045 Uiso 1 1 calc R U . . .
C32 C 0.2783(4) 0.7135(13) 0.9754(5) 0.0412(19) Uani 1 1 d . . . . .
H32 H 0.2626 0.8500 0.9670 0.049 Uiso 1 1 calc R U . . .
C33 C 0.2985(4) 0.6608(14) 1.0401(5) 0.0412(19) Uani 1 1 d . . . . .
H33 H 0.2970 0.7623 1.0764 0.049 Uiso 1 1 calc R U . . .
C34 C 0.3205(4) 0.4684(16) 1.0537(5) 0.041(2) Uani 1 1 d . . . . .
H34 H 0.3349 0.4368 1.0991 0.049 Uiso 1 1 calc R U . . .
C35 C 0.3223(4) 0.3128(14) 1.0011(5) 0.0394(19) Uani 1 1 d . . . . .
H35 H 0.3368 0.1755 1.0108 0.047 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F22 C22 1.414(9) . ?
F2 C2 1.396(10) . ?
F3 C3 1.412(9) . ?
F5 C5 1.408(11) . ?
F6 C6 1.403(10) . ?
F23 C23 1.413(9) . ?
F25 C25 1.398(11) . ?
F26 C26 1.404(9) . ?
O8 C9 1.437(9) . ?
O8 C8 1.446(11) . ?
O28 C28 1.412(11) . ?
O28 C29 1.437(10) . ?
C1 C7 1.515(11) . ?
C1 C6 1.520(12) . ?
C1 C2 1.549(10) . ?
C1 C8 1.559(9) . ?
C2 C3 1.516(11) . ?
C2 H2 1.0000 . ?
C3 C4 1.527(14) . ?
C3 H3 1.0000 . ?
C4 C5 1.492(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.519(11) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.490(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.376(12) . ?
C10 C11 1.375(12) . ?
C11 C12 1.427(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.350(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.402(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.421(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 C26 1.521(11) . ?
C21 C27 1.525(11) . ?
C21 C28 1.554(10) . ?
C21 C22 1.562(11) . ?
C22 C23 1.507(11) . ?
C22 H22 1.0000 . ?
C23 C24 1.520(13) . ?
C23 H23 1.0000 . ?
C24 C25 1.517(14) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.515(11) . ?
C25 H25 1.0000 . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.508(12) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.384(13) . ?
C30 C35 1.416(13) . ?
C31 C32 1.376(13) . ?
C31 H31 0.9500 . ?
C32 C33 1.362(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.345(14) . ?
C33 H33 0.9500 . ?
C34 C35 1.413(14) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O8 C8 113.6(6) . . ?
C28 O28 C29 113.1(6) . . ?
C7 C1 C6 110.6(6) . . ?
C7 C1 C2 109.8(6) . . ?
C6 C1 C2 111.8(7) . . ?
C7 C1 C8 108.2(6) . . ?
C6 C1 C8 108.3(6) . . ?
C2 C1 C8 108.1(6) . . ?
F2 C2 C3 107.4(7) . . ?
F2 C2 C1 110.5(6) . . ?
C3 C2 C1 111.4(6) . . ?
F2 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
F3 C3 C2 108.6(7) . . ?
F3 C3 C4 108.9(8) . . ?
C2 C3 C4 111.9(7) . . ?
F3 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C5 C4 C3 107.9(7) . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
F5 C5 C4 109.7(8) . . ?
F5 C5 C6 108.6(7) . . ?
C4 C5 C6 113.9(7) . . ?
F5 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
F6 C6 C5 107.0(7) . . ?
F6 C6 C1 111.5(6) . . ?
C5 C6 C1 111.7(7) . . ?
F6 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
C1 C6 H6 108.9 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 C1 105.2(6) . . ?
O8 C8 H8A 110.7 . . ?
C1 C8 H8A 110.7 . . ?
O8 C8 H8B 110.7 . . ?
C1 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
O8 C9 C10 107.5(6) . . ?
O8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C15 C10 C11 120.3(8) . . ?
C15 C10 C9 117.4(8) . . ?
C11 C10 C9 122.3(7) . . ?
C10 C11 C12 119.1(8) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 121.4(10) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 119.6(9) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 119.3(9) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C10 C15 C14 120.3(9) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C26 C21 C27 110.3(6) . . ?
C26 C21 C28 110.2(6) . . ?
C27 C21 C28 108.8(7) . . ?
C26 C21 C22 110.5(7) . . ?
C27 C21 C22 108.8(6) . . ?
C28 C21 C22 108.2(6) . . ?
F22 C22 C23 108.3(6) . . ?
F22 C22 C21 109.0(6) . . ?
C23 C22 C21 112.5(6) . . ?
F22 C22 H22 109.0 . . ?
C23 C22 H22 109.0 . . ?
C21 C22 H22 109.0 . . ?
F23 C23 C22 107.3(6) . . ?
F23 C23 C24 110.2(7) . . ?
C22 C23 C24 112.5(7) . . ?
F23 C23 H23 108.9 . . ?
C22 C23 H23 108.9 . . ?
C24 C23 H23 108.9 . . ?
C25 C24 C23 108.3(7) . . ?
C25 C24 H24A 110.0 . . ?
C23 C24 H24A 110.0 . . ?
C25 C24 H24B 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?
F25 C25 C24 109.0(8) . . ?
F25 C25 C26 108.2(7) . . ?
C24 C25 C26 113.0(7) . . ?
F25 C25 H25 108.9 . . ?
C24 C25 H25 108.9 . . ?
C26 C25 H25 108.9 . . ?
F26 C26 C25 107.8(7) . . ?
F26 C26 C21 109.6(6) . . ?
C25 C26 C21 112.6(6) . . ?
F26 C26 H26 108.9 . . ?
C25 C26 H26 108.9 . . ?
C21 C26 H26 108.9 . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O28 C28 C21 107.5(6) . . ?
O28 C28 H28A 110.2 . . ?
C21 C28 H28A 110.2 . . ?
O28 C28 H28B 110.2 . . ?
C21 C28 H28B 110.2 . . ?
H28A C28 H28B 108.5 . . ?
O28 C29 C30 105.8(7) . . ?
O28 C29 H29A 110.6 . . ?
C30 C29 H29A 110.6 . . ?
O28 C29 H29B 110.6 . . ?
C30 C29 H29B 110.6 . . ?
H29A C29 H29B 108.7 . . ?
C31 C30 C35 118.4(8) . . ?
C31 C30 C29 121.1(8) . . ?
C35 C30 C29 120.5(8) . . ?
C32 C31 C30 121.5(8) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C33 C32 C31 119.6(8) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C34 C33 C32 121.6(9) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 C35 120.5(9) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C30 118.4(8) . . ?
C34 C35 H35 120.8 . . ?
C30 C35 H35 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 168.2(7) . . . . ?
C6 C1 C2 F2 -68.7(8) . . . . ?
C8 C1 C2 F2 50.4(9) . . . . ?
C7 C1 C2 C3 -72.5(9) . . . . ?
C6 C1 C2 C3 50.6(9) . . . . ?
C8 C1 C2 C3 169.7(7) . . . . ?
F2 C2 C3 F3 -55.4(9) . . . . ?
C1 C2 C3 F3 -176.5(7) . . . . ?
F2 C2 C3 C4 64.9(8) . . . . ?
C1 C2 C3 C4 -56.3(9) . . . . ?
F3 C3 C4 C5 179.1(7) . . . . ?
C2 C3 C4 C5 59.0(9) . . . . ?
C3 C4 C5 F5 179.7(7) . . . . ?
C3 C4 C5 C6 -58.3(10) . . . . ?
F5 C5 C6 F6 55.1(9) . . . . ?
C4 C5 C6 F6 -67.5(9) . . . . ?
F5 C5 C6 C1 177.3(7) . . . . ?
C4 C5 C6 C1 54.8(10) . . . . ?
C7 C1 C6 F6 -166.6(6) . . . . ?
C2 C1 C6 F6 70.7(8) . . . . ?
C8 C1 C6 F6 -48.2(8) . . . . ?
C7 C1 C6 C5 73.8(8) . . . . ?
C2 C1 C6 C5 -48.9(9) . . . . ?
C8 C1 C6 C5 -167.8(7) . . . . ?
C9 O8 C8 C1 -167.5(6) . . . . ?
C7 C1 C8 O8 -60.6(8) . . . . ?
C6 C1 C8 O8 179.5(6) . . . . ?
C2 C1 C8 O8 58.3(8) . . . . ?
C8 O8 C9 C10 163.3(7) . . . . ?
O8 C9 C10 C15 -68.3(9) . . . . ?
O8 C9 C10 C11 109.5(8) . . . . ?
C15 C10 C11 C12 0.6(11) . . . . ?
C9 C10 C11 C12 -177.2(7) . . . . ?
C10 C11 C12 C13 -0.4(12) . . . . ?
C11 C12 C13 C14 0.1(12) . . . . ?
C12 C13 C14 C15 0.0(12) . . . . ?
C11 C10 C15 C14 -0.4(12) . . . . ?
C9 C10 C15 C14 177.4(7) . . . . ?
C13 C14 C15 C10 0.2(12) . . . . ?
C26 C21 C22 F22 -70.2(7) . . . . ?
C27 C21 C22 F22 168.6(7) . . . . ?
C28 C21 C22 F22 50.5(9) . . . . ?
C26 C21 C22 C23 50.0(8) . . . . ?
C27 C21 C22 C23 -71.2(9) . . . . ?
C28 C21 C22 C23 170.7(7) . . . . ?
F22 C22 C23 F23 -56.0(8) . . . . ?
C21 C22 C23 F23 -176.6(7) . . . . ?
F22 C22 C23 C24 65.4(8) . . . . ?
C21 C22 C23 C24 -55.2(9) . . . . ?
F23 C23 C24 C25 177.2(6) . . . . ?
C22 C23 C24 C25 57.5(9) . . . . ?
C23 C24 C25 F25 -177.9(6) . . . . ?
C23 C24 C25 C26 -57.6(9) . . . . ?
F25 C25 C26 F26 55.6(9) . . . . ?
C24 C25 C26 F26 -65.2(9) . . . . ?
F25 C25 C26 C21 176.6(7) . . . . ?
C24 C25 C26 C21 55.8(10) . . . . ?
C27 C21 C26 F26 -169.4(7) . . . . ?
C28 C21 C26 F26 -49.3(8) . . . . ?
C22 C21 C26 F26 70.2(7) . . . . ?
C27 C21 C26 C25 70.5(9) . . . . ?
C28 C21 C26 C25 -169.4(7) . . . . ?
C22 C21 C26 C25 -49.8(8) . . . . ?
C29 O28 C28 C21 -169.9(7) . . . . ?
C26 C21 C28 O28 178.7(7) . . . . ?
C27 C21 C28 O28 -60.2(8) . . . . ?
C22 C21 C28 O28 57.8(8) . . . . ?
C28 O28 C29 C30 160.5(7) . . . . ?
O28 C29 C30 C31 -71.9(10) . . . . ?
O28 C29 C30 C35 107.7(9) . . . . ?
C35 C30 C31 C32 -1.1(12) . . . . ?
C29 C30 C31 C32 178.6(8) . . . . ?
C30 C31 C32 C33 1.7(13) . . . . ?
C31 C32 C33 C34 -0.5(13) . . . . ?
C32 C33 C34 C35 -1.2(14) . . . . ?
C33 C34 C35 C30 1.7(13) . . . . ?
C31 C30 C35 C34 -0.6(12) . . . . ?
C29 C30 C35 C34 179.8(7) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13a
_database_code_depnum_ccdc_archive 'CCDC 1436754'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-01-09
_audit_creation_method           'by CrystalStructure 4.1'




_chemical_formula_sum            'C8 H12 F4 O'
_chemical_formula_moiety         'C8 H12 F4 O'
_chemical_formula_weight         200.18
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   6.192(5)
_cell_length_b                   13.935(9)
_cell_length_c                   10.252(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.98(2)
_cell_angle_gamma                90.0000
_cell_volume                     846.0(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    566
_cell_measurement_theta_min      24.10
_cell_measurement_theta_max      71.80
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416.00
_exptl_absorpt_coefficient_mu    1.431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.436
_exptl_absorpt_correction_T_max  0.986

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            9216
_diffrn_reflns_av_R_equivalents  0.1355
_diffrn_reflns_theta_max         68.923
_diffrn_reflns_theta_min         5.517
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1562
_reflns_number_gt                1225
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1562
_refine_ls_wR_factor_gt          0.1484
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1562
_refine_ls_number_parameters     123
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1009P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.23459(19) 0.13282(9) 0.89435(11) 0.0379(4) Uani 1 1 d . . . . .
F3 F 0.13605(19) 0.27238(9) 0.69939(12) 0.0406(4) Uani 1 1 d . . . . .
F5 F 0.4153(2) 0.24684(10) 0.51863(11) 0.0431(4) Uani 1 1 d . . . . .
F6 F 0.7024(2) 0.09573(10) 0.59972(12) 0.0463(4) Uani 1 1 d . . . . .
O8 O 0.7729(3) 0.02874(13) 0.92848(16) 0.0502(5) Uani 1 1 d D . . . .
C1 C 0.4678(3) 0.10146(14) 0.74871(18) 0.0316(5) Uani 1 1 d . . . . .
C2 C 0.4131(3) 0.17146(15) 0.85046(18) 0.0302(5) Uani 1 1 d . . . . .
H2 H 0.5494 0.1755 0.9319 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3490(3) 0.27260(15) 0.80076(19) 0.0332(5) Uani 1 1 d . . . . .
H3 H 0.3374 0.3126 0.8794 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5234(3) 0.31710(15) 0.7419(2) 0.0351(5) Uani 1 1 d . . . . .
H4A H 0.6592 0.3335 0.8176 0.042 Uiso 1 1 calc R U . . .
H4B H 0.4617 0.3776 0.6950 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5925(3) 0.25228(16) 0.64207(19) 0.0340(5) Uani 1 1 d . . . . .
H5 H 0.7283 0.2805 0.6226 0.041 Uiso 1 1 calc R U . . .
C6 C 0.6509(3) 0.15241(15) 0.69955(19) 0.0325(5) Uani 1 1 d . . . . .
H6 H 0.7901 0.1572 0.7789 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2578(4) 0.07262(17) 0.6316(2) 0.0405(6) Uani 1 1 d . . . . .
H7A H 0.3046 0.0340 0.5647 0.049 Uiso 1 1 calc R U . . .
H7B H 0.1803 0.1305 0.5873 0.049 Uiso 1 1 calc R U . . .
H7C H 0.1552 0.0350 0.6684 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5680(4) 0.00890(16) 0.8232(2) 0.0399(5) Uani 1 1 d . . . . .
H8A H 0.4575 -0.0210 0.8638 0.048 Uiso 1 1 calc R U . . .
H8B H 0.5989 -0.0370 0.7572 0.048 Uiso 1 1 calc R U . . .
H8O H 0.802(7) -0.0279(17) 0.987(3) 0.102(12) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.416(2) . ?
F3 C3 1.421(2) . ?
F5 C5 1.414(2) . ?
F6 C6 1.401(2) . ?
O8 C8 1.432(3) . ?
O8 H8O 0.979(5) . ?
C1 C8 1.535(3) . ?
C1 C2 1.536(3) . ?
C1 C6 1.542(3) . ?
C1 C7 1.544(3) . ?
C2 C3 1.512(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.515(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.518(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.513(3) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O8 H8O 106(2) . . ?
C8 C1 C2 109.43(16) . . ?
C8 C1 C6 108.72(17) . . ?
C2 C1 C6 104.98(16) . . ?
C8 C1 C7 107.14(17) . . ?
C2 C1 C7 113.01(17) . . ?
C6 C1 C7 113.48(16) . . ?
F2 C2 C3 108.00(16) . . ?
F2 C2 C1 108.77(16) . . ?
C3 C2 C1 116.82(16) . . ?
F2 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
C1 C2 H2 107.6 . . ?
F3 C3 C2 109.92(16) . . ?
F3 C3 C4 109.08(16) . . ?
C2 C3 C4 111.62(17) . . ?
F3 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
C3 C4 C5 113.52(18) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
F5 C5 C6 109.51(16) . . ?
F5 C5 C4 109.73(17) . . ?
C6 C5 C4 111.53(16) . . ?
F5 C5 H5 108.7 . . ?
C6 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
F6 C6 C5 108.27(16) . . ?
F6 C6 C1 108.96(17) . . ?
C5 C6 C1 115.84(17) . . ?
F6 C6 H6 107.8 . . ?
C5 C6 H6 107.8 . . ?
C1 C6 H6 107.8 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 C1 110.68(18) . . ?
O8 C8 H8A 109.5 . . ?
C1 C8 H8A 109.5 . . ?
O8 C8 H8B 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 F2 -67.3(2) . . . . ?
C6 C1 C2 F2 176.21(14) . . . . ?
C7 C1 C2 F2 52.0(2) . . . . ?
C8 C1 C2 C3 170.23(16) . . . . ?
C6 C1 C2 C3 53.7(2) . . . . ?
C7 C1 C2 C3 -70.5(2) . . . . ?
F2 C2 C3 F3 -54.61(19) . . . . ?
C1 C2 C3 F3 68.3(2) . . . . ?
F2 C2 C3 C4 -175.79(15) . . . . ?
C1 C2 C3 C4 -52.9(2) . . . . ?
F3 C3 C4 C5 -73.9(2) . . . . ?
C2 C3 C4 C5 47.8(2) . . . . ?
C3 C4 C5 F5 72.7(2) . . . . ?
C3 C4 C5 C6 -48.9(2) . . . . ?
F5 C5 C6 F6 55.6(2) . . . . ?
C4 C5 C6 F6 177.24(16) . . . . ?
F5 C5 C6 C1 -67.1(2) . . . . ?
C4 C5 C6 C1 54.6(2) . . . . ?
C8 C1 C6 F6 66.3(2) . . . . ?
C2 C1 C6 F6 -176.65(14) . . . . ?
C7 C1 C6 F6 -52.8(2) . . . . ?
C8 C1 C6 C5 -171.34(16) . . . . ?
C2 C1 C6 C5 -54.3(2) . . . . ?
C7 C1 C6 C5 69.6(2) . . . . ?
C2 C1 C8 O8 -60.9(2) . . . . ?
C6 C1 C8 O8 53.2(2) . . . . ?
C7 C1 C8 O8 176.24(16) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_13b
_database_code_depnum_ccdc_archive 'CCDC 1436755'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-01-23
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C8 H12 F4 O'
_chemical_formula_moiety         'C8 H12 F4 O'
_chemical_formula_weight         200.18
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
_space_group_IT_number           60
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,-Y,1/2+Z
4 1/2-X,1/2-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,+Y,1/2-Z
8 1/2+X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   18.859(13)
_cell_length_b                   10.647(7)
_cell_length_c                   8.927(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1792(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    685
_cell_measurement_theta_min      24.20
_cell_measurement_theta_max      72.90
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832.00
_exptl_absorpt_coefficient_mu    1.351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.325
_exptl_absorpt_correction_T_max  0.960

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            16769
_diffrn_reflns_av_R_equivalents  0.1982
_diffrn_reflns_theta_max         69.284
_diffrn_reflns_theta_min         4.690
_diffrn_reflns_theta_full        68.500
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1661
_reflns_number_gt                1003
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.1118
_refine_ls_wR_factor_ref         0.3346
_refine_ls_wR_factor_gt          0.3106
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1661
_refine_ls_number_parameters     123
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1899P)²+1.2932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.22622(18) 0.7574(4) 0.1369(4) 0.0709(12) Uani 1 1 d . . . . .
F3 F 0.28029(18) 0.6019(4) -0.0726(5) 0.0820(13) Uani 1 1 d . . . . .
F5 F 0.06196(19) 0.4481(3) 0.1127(4) 0.0703(12) Uani 1 1 d . . . . .
F6 F 0.09721(18) 0.6643(3) 0.2459(4) 0.0625(11) Uani 1 1 d . . . . .
O8 O 0.0294(3) 0.9318(4) 0.1145(6) 0.0745(14) Uani 1 1 d D . . . .
C1 C 0.1129(3) 0.7764(5) 0.0158(6) 0.0455(13) Uani 1 1 d . . . . .
C2 C 0.1926(3) 0.7506(6) -0.0014(7) 0.0549(15) Uani 1 1 d . . . . .
H2 H 0.2133 0.8163 -0.0684 0.066 Uiso 1 1 calc R U . . .
C3 C 0.2075(3) 0.6231(6) -0.0688(7) 0.0544(14) Uani 1 1 d . . . . .
H3 H 0.1888 0.6215 -0.1736 0.065 Uiso 1 1 calc R U . . .
C4 C 0.1725(3) 0.5189(6) 0.0199(7) 0.0586(15) Uani 1 1 d . . . . .
H4A H 0.1819 0.4369 -0.0285 0.070 Uiso 1 1 calc R U . . .
H4B H 0.1923 0.5165 0.1227 0.070 Uiso 1 1 calc R U . . .
C5 C 0.0948(3) 0.5422(5) 0.0261(7) 0.0539(15) Uani 1 1 d . . . . .
H5 H 0.0752 0.5390 -0.0779 0.065 Uiso 1 1 calc R U . . .
C6 C 0.0759(3) 0.6680(5) 0.0955(7) 0.0502(14) Uani 1 1 d . . . . .
H6 H 0.0234 0.6805 0.0904 0.060 Uiso 1 1 calc R U . . .
C7 C 0.0806(3) 0.7957(5) -0.1387(7) 0.0561(14) Uani 1 1 d . . . . .
H7A H 0.1090 0.8569 -0.1948 0.067 Uiso 1 1 calc R U . . .
H7B H 0.0320 0.8272 -0.1282 0.067 Uiso 1 1 calc R U . . .
H7C H 0.0800 0.7156 -0.1928 0.067 Uiso 1 1 calc R U . . .
C8 C 0.1022(3) 0.8989(5) 0.1063(7) 0.0560(15) Uani 1 1 d . . . . .
H8A H 0.1211 0.8876 0.2088 0.067 Uiso 1 1 calc R U . . .
H8B H 0.1289 0.9680 0.0580 0.067 Uiso 1 1 calc R U . . .
H8O H -0.018(4) 0.911(16) 0.078(19) 0.23(8) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SHELXD2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.390(7) . ?
F3 C3 1.391(6) . ?
F5 C5 1.409(6) . ?
F6 C6 1.402(7) . ?
O8 C8 1.418(8) . ?
O8 H8O 0.980(5) . ?
C1 C7 1.523(8) . ?
C1 C6 1.525(8) . ?
C1 C2 1.535(9) . ?
C1 C8 1.547(8) . ?
C2 C3 1.512(9) . ?
C2 H2 1.0000 . ?
C3 C4 1.515(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.488(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(8) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O8 H8O 144(10) . . ?
C7 C1 C6 110.0(4) . . ?
C7 C1 C2 109.0(5) . . ?
C6 C1 C2 111.0(4) . . ?
C7 C1 C8 107.8(4) . . ?
C6 C1 C8 109.6(5) . . ?
C2 C1 C8 109.4(4) . . ?
F2 C2 C3 108.4(5) . . ?
F2 C2 C1 110.4(5) . . ?
C3 C2 C1 112.5(5) . . ?
F2 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
F3 C3 C2 109.8(5) . . ?
F3 C3 C4 108.9(4) . . ?
C2 C3 C4 111.6(5) . . ?
F3 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
C5 C4 C3 109.1(5) . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
F5 C5 C4 109.6(4) . . ?
F5 C5 C6 107.5(5) . . ?
C4 C5 C6 113.2(5) . . ?
F5 C5 H5 108.8 . . ?
C4 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
F6 C6 C5 107.4(4) . . ?
F6 C6 C1 109.7(4) . . ?
C5 C6 C1 111.7(5) . . ?
F6 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C1 C6 H6 109.3 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 C1 111.2(4) . . ?
O8 C8 H8A 109.4 . . ?
C1 C8 H8A 109.4 . . ?
O8 C8 H8B 109.4 . . ?
C1 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 168.1(4) . . . . ?
C6 C1 C2 F2 -70.5(6) . . . . ?
C8 C1 C2 F2 50.5(6) . . . . ?
C7 C1 C2 C3 -70.6(6) . . . . ?
C6 C1 C2 C3 50.7(6) . . . . ?
C8 C1 C2 C3 171.7(5) . . . . ?
F2 C2 C3 F3 -53.8(6) . . . . ?
C1 C2 C3 F3 -176.2(4) . . . . ?
F2 C2 C3 C4 67.1(6) . . . . ?
C1 C2 C3 C4 -55.3(6) . . . . ?
F3 C3 C4 C5 179.2(5) . . . . ?
C2 C3 C4 C5 57.8(6) . . . . ?
C3 C4 C5 F5 -178.1(5) . . . . ?
C3 C4 C5 C6 -58.1(7) . . . . ?
F5 C5 C6 F6 56.0(6) . . . . ?
C4 C5 C6 F6 -65.1(6) . . . . ?
F5 C5 C6 C1 176.3(4) . . . . ?
C4 C5 C6 C1 55.2(6) . . . . ?
C7 C1 C6 F6 -169.9(4) . . . . ?
C2 C1 C6 F6 69.3(5) . . . . ?
C8 C1 C6 F6 -51.5(6) . . . . ?
C7 C1 C6 C5 71.0(6) . . . . ?
C2 C1 C6 C5 -49.7(6) . . . . ?
C8 C1 C6 C5 -170.6(5) . . . . ?
C7 C1 C8 O8 56.9(6) . . . . ?
C6 C1 C8 O8 -62.8(6) . . . . ?
C2 C1 C8 O8 175.3(5) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_16
_database_code_depnum_ccdc_archive 'CCDC 1436756'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-05-21
_audit_creation_method           'by CrystalStructure 4.1'

_chemical_formula_sum            'C21 H26 F4 N2 O2'
_chemical_formula_moiety         'C21 H26 F4 N2 O2'
_chemical_formula_weight         414.44
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.4475(14)
_cell_length_b                   11.766(2)
_cell_length_c                   16.901(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.766(3)
_cell_angle_gamma                90.0000
_cell_volume                     2041.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2304
_cell_measurement_theta_min      24.10
_cell_measurement_theta_max      74.60
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872.00
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.492
_exptl_absorpt_correction_T_max  0.972

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            21887
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_min         4.606
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3691
_reflns_number_gt                3644
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1067
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3691
_refine_ls_number_parameters     268
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0435P)²+0.8177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.39427(8) 0.20411(8) 0.59531(5) 0.0348(2) Uani 1 1 d . . . . .
F3 F 0.44564(7) 0.36055(8) 0.48791(5) 0.0369(2) Uani 1 1 d . . . . .
F5 F 0.25151(9) 0.52311(8) 0.69464(5) 0.0437(3) Uani 1 1 d . . . . .
F6 F 0.27085(8) 0.29804(8) 0.71352(5) 0.0350(2) Uani 1 1 d . . . . .
O9 O 0.05641(10) 0.13446(8) 0.41820(6) 0.0283(2) Uani 1 1 d . . . . .
O22 O -0.08021(8) 0.45502(7) 0.57539(5) 0.0244(2) Uani 1 1 d . . . . .
N10 N 0.04243(10) 0.31556(9) 0.37054(6) 0.0220(2) Uani 1 1 d D . . . .
N18 N -0.07967(10) 0.27135(8) 0.53627(6) 0.0199(2) Uani 1 1 d . . . . .
C1 C 0.16634(12) 0.25195(11) 0.57810(7) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.29068(12) 0.25177(11) 0.54043(8) 0.0248(3) Uani 1 1 d . . . . .
H2 H 0.2745 0.2048 0.4902 0.030 Uiso 1 1 calc R U . . .
C3 C 0.33202(12) 0.36981(12) 0.52039(8) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.2616 0.4043 0.4792 0.032 Uiso 1 1 calc R U . . .
C4 C 0.35752(13) 0.44577(13) 0.59383(9) 0.0331(3) Uani 1 1 d . . . . .
H4A H 0.3856 0.5220 0.5792 0.040 Uiso 1 1 calc R U . . .
H4B H 0.4272 0.4130 0.6354 0.040 Uiso 1 1 calc R U . . .
C5 C 0.23133(13) 0.45456(12) 0.62594(8) 0.0292(3) Uani 1 1 d . . . . .
H5 H 0.1635 0.4907 0.5839 0.035 Uiso 1 1 calc R U . . .
C6 C 0.18171(12) 0.33967(12) 0.64772(8) 0.0254(3) Uani 1 1 d . . . . .
H6 H 0.0954 0.3503 0.6642 0.031 Uiso 1 1 calc R U . . .
C7 C 0.14648(14) 0.13341(12) 0.61095(9) 0.0294(3) Uani 1 1 d . . . . .
H7A H 0.1354 0.0782 0.5668 0.035 Uiso 1 1 calc R U . . .
H7B H 0.0686 0.1334 0.6355 0.035 Uiso 1 1 calc R U . . .
H7C H 0.2227 0.1127 0.6516 0.035 Uiso 1 1 calc R U . . .
C8 C 0.04735(11) 0.29058(10) 0.51189(7) 0.0191(3) Uani 1 1 d . . . . .
H8 H 0.0561 0.3746 0.5055 0.023 Uiso 1 1 calc R U . . .
C9 C 0.04876(11) 0.23752(10) 0.42874(7) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.04979(13) 0.28868(12) 0.28692(8) 0.0270(3) Uani 1 1 d . . . . .
H11A H -0.0315 0.3132 0.2510 0.032 Uiso 1 1 calc R U . . .
H11B H 0.0587 0.2055 0.2809 0.032 Uiso 1 1 calc R U . . .
C12 C 0.16512(13) 0.34832(11) 0.26313(7) 0.0245(3) Uani 1 1 d . . . . .
C13 C 0.14635(14) 0.43423(11) 0.20557(8) 0.0286(3) Uani 1 1 d . . . . .
H13 H 0.0606 0.4550 0.1803 0.034 Uiso 1 1 calc R U . . .
C14 C 0.25326(16) 0.48992(12) 0.18499(9) 0.0337(3) Uani 1 1 d . . . . .
H14 H 0.2398 0.5485 0.1456 0.040 Uiso 1 1 calc R U . . .
C15 C 0.37868(15) 0.46072(12) 0.22136(9) 0.0326(3) Uani 1 1 d . . . . .
H15 H 0.4511 0.4991 0.2072 0.039 Uiso 1 1 calc R U . . .
C16 C 0.39804(14) 0.37501(12) 0.27868(9) 0.0323(3) Uani 1 1 d . . . . .
H16 H 0.4839 0.3542 0.3037 0.039 Uiso 1 1 calc R U . . .
C17 C 0.29160(14) 0.31974(11) 0.29934(8) 0.0285(3) Uani 1 1 d . . . . .
H17 H 0.3054 0.2614 0.3389 0.034 Uiso 1 1 calc R U . . .
C19 C -0.15231(13) 0.16372(11) 0.51557(8) 0.0252(3) Uani 1 1 d . . . . .
H19A H -0.1975 0.1431 0.5601 0.030 Uiso 1 1 calc R U . . .
H19B H -0.0896 0.1023 0.5104 0.030 Uiso 1 1 calc R U . . .
C20 C -0.25078(14) 0.17173(12) 0.43860(9) 0.0333(3) Uani 1 1 d . . . . .
H20 H -0.2219 0.1971 0.3915 0.040 Uiso 1 1 calc R U . . .
C21 C -0.37464(17) 0.14565(15) 0.43279(13) 0.0496(4) Uani 1 1 d . . . . .
H21A H -0.4062 0.1201 0.4789 0.059 Uiso 1 1 calc R U . . .
H21B H -0.4325 0.1524 0.3825 0.059 Uiso 1 1 calc R U . . .
C22 C -0.13454(12) 0.36090(10) 0.56821(7) 0.0206(3) Uani 1 1 d . . . . .
C23 C -0.26078(13) 0.34323(12) 0.59725(8) 0.0276(3) Uani 1 1 d . . . . .
H23A H -0.2863 0.4142 0.6204 0.033 Uiso 1 1 calc R U . . .
H23B H -0.2495 0.2835 0.6384 0.033 Uiso 1 1 calc R U . . .
H23C H -0.3288 0.3206 0.5519 0.033 Uiso 1 1 calc R U . . .
H10 H 0.0447(17) 0.3955(6) 0.3856(11) 0.039(4) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.4040(15) . ?
F3 C3 1.4021(14) . ?
F5 C5 1.3971(15) . ?
F6 C6 1.3989(15) . ?
O9 C9 1.2304(16) . ?
O22 C22 1.2400(16) . ?
N10 C9 1.3382(17) . ?
N10 C11 1.4641(16) . ?
N10 H10 0.974(5) . ?
N18 C22 1.3585(16) . ?
N18 C8 1.4786(15) . ?
N18 C19 1.4843(16) . ?
C1 C7 1.5296(18) . ?
C1 C2 1.5498(17) . ?
C1 C6 1.5508(18) . ?
C1 C8 1.5762(17) . ?
C2 C3 1.512(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.512(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.5200(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(2) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5404(16) . ?
C8 H8 1.0000 . ?
C11 C12 1.5122(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3911(19) . ?
C12 C17 1.390(2) . ?
C13 C14 1.394(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.503(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.316(2) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C22 C23 1.5051(17) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N10 C11 123.85(11) . . ?
C9 N10 H10 118.4(11) . . ?
C11 N10 H10 117.3(11) . . ?
C22 N18 C8 117.35(10) . . ?
C22 N18 C19 121.35(10) . . ?
C8 N18 C19 120.72(9) . . ?
C7 C1 C2 109.19(10) . . ?
C7 C1 C6 109.47(10) . . ?
C2 C1 C6 109.67(10) . . ?
C7 C1 C8 112.22(10) . . ?
C2 C1 C8 108.62(9) . . ?
C6 C1 C8 107.63(9) . . ?
F2 C2 C3 107.32(10) . . ?
F2 C2 C1 109.33(10) . . ?
C3 C2 C1 112.78(10) . . ?
F2 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
F3 C3 C4 109.58(10) . . ?
F3 C3 C2 108.33(11) . . ?
C4 C3 C2 111.90(11) . . ?
F3 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C3 C4 C5 107.56(11) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
F5 C5 C4 109.26(11) . . ?
F5 C5 C6 108.55(11) . . ?
C4 C5 C6 112.60(12) . . ?
F5 C5 H5 108.8 . . ?
C4 C5 H5 108.8 . . ?
C6 C5 H5 108.8 . . ?
F6 C6 C5 107.33(11) . . ?
F6 C6 C1 109.23(10) . . ?
C5 C6 C1 113.61(10) . . ?
F6 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
C1 C6 H6 108.9 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N18 C8 C9 110.75(9) . . ?
N18 C8 C1 112.82(9) . . ?
C9 C8 C1 112.96(9) . . ?
N18 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C1 C8 H8 106.6 . . ?
O9 C9 N10 124.43(11) . . ?
O9 C9 C8 122.92(11) . . ?
N10 C9 C8 112.64(10) . . ?
N10 C11 C12 110.15(10) . . ?
N10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C17 118.81(12) . . ?
C13 C12 C11 120.53(13) . . ?
C17 C12 C11 120.65(12) . . ?
C12 C13 C14 120.09(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.61(13) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.58(13) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 119.82(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 121.09(13) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
N18 C19 C20 112.81(11) . . ?
N18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 123.69(16) . . ?
C21 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
O22 C22 N18 120.81(11) . . ?
O22 C22 C23 120.29(11) . . ?
N18 C22 C23 118.88(11) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 -50.00(14) . . . . ?
C6 C1 C2 F2 69.94(13) . . . . ?
C8 C1 C2 F2 -172.68(10) . . . . ?
C7 C1 C2 C3 -169.32(11) . . . . ?
C6 C1 C2 C3 -49.38(14) . . . . ?
C8 C1 C2 C3 68.01(13) . . . . ?
F2 C2 C3 F3 58.71(12) . . . . ?
C1 C2 C3 F3 179.18(10) . . . . ?
F2 C2 C3 C4 -62.20(13) . . . . ?
C1 C2 C3 C4 58.28(14) . . . . ?
F3 C3 C4 C5 179.14(11) . . . . ?
C2 C3 C4 C5 -60.68(15) . . . . ?
C3 C4 C5 F5 179.25(11) . . . . ?
C3 C4 C5 C6 58.56(15) . . . . ?
F5 C5 C6 F6 -54.31(13) . . . . ?
C4 C5 C6 F6 66.78(13) . . . . ?
F5 C5 C6 C1 -175.17(10) . . . . ?
C4 C5 C6 C1 -54.08(14) . . . . ?
C7 C1 C6 F6 47.42(13) . . . . ?
C2 C1 C6 F6 -72.36(13) . . . . ?
C8 C1 C6 F6 169.65(9) . . . . ?
C7 C1 C6 C5 167.20(11) . . . . ?
C2 C1 C6 C5 47.43(14) . . . . ?
C8 C1 C6 C5 -70.57(13) . . . . ?
C22 N18 C8 C9 -135.33(11) . . . . ?
C19 N18 C8 C9 36.01(14) . . . . ?
C22 N18 C8 C1 96.93(12) . . . . ?
C19 N18 C8 C1 -91.73(13) . . . . ?
C7 C1 C8 N18 47.45(13) . . . . ?
C2 C1 C8 N18 168.27(10) . . . . ?
C6 C1 C8 N18 -73.06(12) . . . . ?
C7 C1 C8 C9 -79.12(12) . . . . ?
C2 C1 C8 C9 41.70(13) . . . . ?
C6 C1 C8 C9 160.38(10) . . . . ?
C11 N10 C9 O9 -2.91(19) . . . . ?
C11 N10 C9 C8 176.31(11) . . . . ?
N18 C8 C9 O9 -73.94(14) . . . . ?
C1 C8 C9 O9 53.72(15) . . . . ?
N18 C8 C9 N10 106.82(11) . . . . ?
C1 C8 C9 N10 -125.52(11) . . . . ?
C9 N10 C11 C12 -119.97(13) . . . . ?
N10 C11 C12 C13 -113.09(13) . . . . ?
N10 C11 C12 C17 65.77(16) . . . . ?
C17 C12 C13 C14 0.10(19) . . . . ?
C11 C12 C13 C14 178.98(12) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C12 0.4(2) . . . . ?
C13 C12 C17 C16 -0.27(19) . . . . ?
C11 C12 C17 C16 -179.15(12) . . . . ?
C22 N18 C19 C20 76.94(15) . . . . ?
C8 N18 C19 C20 -94.05(13) . . . . ?
N18 C19 C20 C21 -126.30(15) . . . . ?
C8 N18 C22 O22 0.90(16) . . . . ?
C19 N18 C22 O22 -170.38(11) . . . . ?
C8 N18 C22 C23 -177.23(10) . . . . ?
C19 N18 C22 C23 11.49(17) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_17
_database_code_depnum_ccdc_archive 'CCDC 1436757'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-15
_audit_creation_method           'by CrystalStructure 4.1'



_chemical_formula_sum            'C26 H28 F4 N2 O2'
_chemical_formula_moiety         'C26 H28 F4 N2 O2'
_chemical_formula_weight         476.51
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   12.108(3)
_cell_length_b                   13.669(4)
_cell_length_c                   16.043(4)
_cell_angle_alpha                102.251(3)
_cell_angle_beta                 91.947(5)
_cell_angle_gamma                114.376(5)
_cell_volume                     2341.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4364
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000.00
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            30851
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_theta_max         25.435
_diffrn_reflns_theta_min         2.128
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             8599
_reflns_number_gt                5930
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1483
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         8599
_refine_ls_number_parameters     623
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0927P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.16
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.77759(11) 0.16288(10) 0.07806(9) 0.0280(3) Uani 1 1 d . . . . .
F3 F 0.82034(12) 0.37856(11) 0.10047(9) 0.0300(3) Uani 1 1 d . . . . .
F5 F 1.06352(12) 0.52291(10) 0.20464(10) 0.0338(3) Uani 1 1 d . . . . .
F6 F 1.16995(12) 0.39667(11) 0.24571(10) 0.0378(4) Uani 1 1 d . . . . .
F32 F 0.79225(12) 0.01759(11) 0.49767(10) 0.0344(3) Uani 1 1 d . . . . .
F33 F 1.02228(13) 0.14128(12) 0.58203(9) 0.0355(3) Uani 1 1 d . . . . .
F35 F 1.08089(12) 0.37292(11) 0.60508(10) 0.0368(4) Uani 1 1 d . . . . .
F36 F 0.89402(12) 0.40188(11) 0.53163(10) 0.0357(4) Uani 1 1 d . . . . .
O9 O 0.94274(14) 0.13410(13) 0.28560(11) 0.0283(4) Uani 1 1 d . . . . .
O22 O 1.08474(13) 0.11385(12) -0.00410(10) 0.0254(4) Uani 1 1 d . . . . .
O39 O 0.73357(15) 0.21358(14) 0.33212(11) 0.0344(4) Uani 1 1 d . . . . .
O52 O 0.52004(15) 0.11232(13) 0.57546(11) 0.0332(4) Uani 1 1 d . . . . .
N10 N 0.89354(17) -0.01697(15) 0.17636(13) 0.0245(4) Uani 1 1 d D . . . .
N18 N 1.12361(16) 0.17680(15) 0.14170(12) 0.0228(4) Uani 1 1 d . . . . .
N40 N 0.60139(17) 0.03904(16) 0.32749(13) 0.0267(4) Uani 1 1 d D . . . .
N48 N 0.63185(17) 0.23785(16) 0.50355(13) 0.0270(5) Uani 1 1 d . . . . .
C1 C 0.98006(19) 0.27078(18) 0.15490(15) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.84310(19) 0.23875(18) 0.15609(15) 0.0232(5) Uani 1 1 d . . . . .
H2 H 0.8174 0.1997 0.2031 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8047(2) 0.33165(18) 0.17144(15) 0.0246(5) Uani 1 1 d . . . . .
H3 H 0.7159 0.3006 0.1783 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8759(2) 0.41985(19) 0.25235(16) 0.0270(5) Uani 1 1 d . . . . .
H4A H 0.8604 0.4858 0.2537 0.032 Uiso 1 1 calc R U . . .
H4B H 0.8450 0.3917 0.3029 0.032 Uiso 1 1 calc R U . . .
C5 C 1.0117(2) 0.45471(19) 0.26020(16) 0.0280(5) Uani 1 1 d . . . . .
H5 H 1.0483 0.4985 0.3206 0.034 Uiso 1 1 calc R U . . .
C6 C 1.04243(19) 0.35600(18) 0.24109(16) 0.0255(5) Uani 1 1 d . . . . .
H6 H 1.0170 0.3167 0.2880 0.031 Uiso 1 1 calc R U . . .
C7 C 1.0280(2) 0.3184(2) 0.07789(16) 0.0281(5) Uani 1 1 d . . . . .
H7A H 1.0134 0.3842 0.0797 0.034 Uiso 1 1 calc R U . . .
H7B H 0.9850 0.2624 0.0241 0.034 Uiso 1 1 calc R U . . .
H7C H 1.1160 0.3389 0.0807 0.034 Uiso 1 1 calc R U . . .
C8 C 0.99642(19) 0.16103(18) 0.14445(15) 0.0225(5) Uani 1 1 d . . . . .
H8 H 0.9512 0.1133 0.0866 0.027 Uiso 1 1 calc R U . . .
C9 C 0.94074(19) 0.09172(19) 0.20904(15) 0.0225(5) Uani 1 1 d . . . . .
C11 C 0.8513(2) -0.09382(19) 0.23237(16) 0.0289(5) Uani 1 1 d . . . . .
H11A H 0.7779 -0.0912 0.2562 0.035 Uiso 1 1 calc R U . . .
H11B H 0.9161 -0.0719 0.2810 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8209(2) -0.20940(19) 0.18068(16) 0.0259(5) Uani 1 1 d . . . . .
C13 C 0.7107(2) -0.2713(2) 0.12663(17) 0.0292(5) Uani 1 1 d . . . . .
H13 H 0.6526 -0.2416 0.1238 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6849(2) -0.3760(2) 0.07682(18) 0.0337(6) Uani 1 1 d . . . . .
H14 H 0.6095 -0.4177 0.0396 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7680(2) -0.4202(2) 0.08089(18) 0.0331(6) Uani 1 1 d . . . . .
H15 H 0.7501 -0.4922 0.0467 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8776(2) -0.3595(2) 0.13497(18) 0.0336(6) Uani 1 1 d . . . . .
H16 H 0.9351 -0.3898 0.1381 0.040 Uiso 1 1 calc R U . . .
C17 C 0.9037(2) -0.2544(2) 0.18476(17) 0.0298(6) Uani 1 1 d . . . . .
H17 H 0.9790 -0.2130 0.2220 0.036 Uiso 1 1 calc R U . . .
C19 C 1.1988(2) 0.1899(2) 0.22103(15) 0.0273(5) Uani 1 1 d . . . . .
H19A H 1.1721 0.2266 0.2710 0.033 Uiso 1 1 calc R U . . .
H19B H 1.2853 0.2389 0.2187 0.033 Uiso 1 1 calc R U . . .
C20 C 1.1909(2) 0.0825(2) 0.23431(17) 0.0335(6) Uani 1 1 d . . . . .
H20 H 1.1859 0.0275 0.1849 0.040 Uiso 1 1 calc R U . . .
C21 C 1.1904(2) 0.0586(2) 0.30952(19) 0.0423(7) Uani 1 1 d . . . . .
H21A H 1.1952 0.1116 0.3603 0.051 Uiso 1 1 calc R U . . .
H21B H 1.1851 -0.0116 0.3131 0.051 Uiso 1 1 calc R U . . .
C22 C 1.1569(2) 0.15068(18) 0.06326(15) 0.0228(5) Uani 1 1 d . . . . .
C23 C 1.2876(2) 0.17225(18) 0.05763(15) 0.0228(5) Uani 1 1 d . . . . .
C24 C 1.3828(2) 0.27818(19) 0.08569(16) 0.0274(5) Uani 1 1 d . . . . .
H24 H 1.3668 0.3378 0.1157 0.033 Uiso 1 1 calc R U . . .
C25 C 1.5003(2) 0.2968(2) 0.07000(17) 0.0326(6) Uani 1 1 d . . . . .
H25 H 1.5651 0.3692 0.0894 0.039 Uiso 1 1 calc R U . . .
C26 C 1.5242(2) 0.2107(2) 0.02629(17) 0.0315(6) Uani 1 1 d . . . . .
H26 H 1.6048 0.2239 0.0147 0.038 Uiso 1 1 calc R U . . .
C27 C 1.4307(2) 0.1057(2) -0.00045(16) 0.0303(6) Uani 1 1 d . . . . .
H27 H 1.4472 0.0460 -0.0295 0.036 Uiso 1 1 calc R U . . .
C28 C 1.3131(2) 0.0865(2) 0.01466(16) 0.0262(5) Uani 1 1 d . . . . .
H28 H 1.2490 0.0138 -0.0046 0.031 Uiso 1 1 calc R U . . .
C31 C 0.8245(2) 0.20550(19) 0.51267(15) 0.0266(5) Uani 1 1 d . . . . .
C32 C 0.8646(2) 0.11482(19) 0.47346(16) 0.0277(5) Uani 1 1 d . . . . .
H32 H 0.8471 0.0990 0.4094 0.033 Uiso 1 1 calc R U . . .
C33 C 0.9973(2) 0.1391(2) 0.49518(16) 0.0303(5) Uani 1 1 d . . . . .
H33 H 1.0128 0.0785 0.4583 0.036 Uiso 1 1 calc R U . . .
C34 C 1.0817(2) 0.2475(2) 0.47756(17) 0.0310(6) Uani 1 1 d . . . . .
H34A H 1.0786 0.2383 0.4145 0.037 Uiso 1 1 calc R U . . .
H34B H 1.1665 0.2666 0.5014 0.037 Uiso 1 1 calc R U . . .
C35 C 1.0502(2) 0.3421(2) 0.51553(16) 0.0307(6) Uani 1 1 d . . . . .
H35 H 1.1000 0.4068 0.4923 0.037 Uiso 1 1 calc R U . . .
C36 C 0.9167(2) 0.31191(19) 0.49134(16) 0.0283(5) Uani 1 1 d . . . . .
H36 H 0.9022 0.3021 0.4277 0.034 Uiso 1 1 calc R U . . .
C37 C 0.8219(2) 0.2199(2) 0.61022(16) 0.0298(5) Uani 1 1 d . . . . .
H37A H 0.9034 0.2388 0.6388 0.036 Uiso 1 1 calc R U . . .
H37B H 0.7628 0.1506 0.6212 0.036 Uiso 1 1 calc R U . . .
H37C H 0.7977 0.2795 0.6328 0.036 Uiso 1 1 calc R U . . .
C38 C 0.6901(2) 0.16538(19) 0.46821(15) 0.0256(5) Uani 1 1 d . . . . .
H38 H 0.6410 0.0926 0.4815 0.031 Uiso 1 1 calc R U . . .
C39 C 0.6773(2) 0.1419(2) 0.36957(16) 0.0268(5) Uani 1 1 d . . . . .
C41 C 0.5799(2) 0.0069(2) 0.23354(16) 0.0299(5) Uani 1 1 d . . . . .
H41A H 0.6465 -0.0110 0.2116 0.036 Uiso 1 1 calc R U . . .
H41B H 0.5816 0.0701 0.2119 0.036 Uiso 1 1 calc R U . . .
C42 C 0.4589(2) -0.0918(2) 0.19973(15) 0.0264(5) Uani 1 1 d . . . . .
C43 C 0.4413(2) -0.1971(2) 0.20412(17) 0.0309(6) Uani 1 1 d . . . . .
H43 H 0.5058 -0.2077 0.2301 0.037 Uiso 1 1 calc R U . . .
C44 C 0.3301(2) -0.2871(2) 0.17087(18) 0.0360(6) Uani 1 1 d . . . . .
H44 H 0.3184 -0.3592 0.1744 0.043 Uiso 1 1 calc R U . . .
C45 C 0.2357(2) -0.2724(2) 0.13237(17) 0.0368(6) Uani 1 1 d . . . . .
H45 H 0.1597 -0.3343 0.1090 0.044 Uiso 1 1 calc R U . . .
C46 C 0.2525(2) -0.1687(2) 0.12816(17) 0.0349(6) Uani 1 1 d . . . . .
H46 H 0.1878 -0.1585 0.1021 0.042 Uiso 1 1 calc R U . . .
C47 C 0.3631(2) -0.0783(2) 0.16156(16) 0.0303(6) Uani 1 1 d . . . . .
H47 H 0.3736 -0.0064 0.1584 0.036 Uiso 1 1 calc R U . . .
C49 C 0.6367(2) 0.3279(2) 0.46472(17) 0.0332(6) Uani 1 1 d . . . . .
H49A H 0.7082 0.3495 0.4329 0.040 Uiso 1 1 calc R U . . .
H49B H 0.6484 0.3934 0.5111 0.040 Uiso 1 1 calc R U . . .
C50 C 0.5233(3) 0.2954(3) 0.4046(2) 0.0562(9) Uani 1 1 d . . . . .
H50 H 0.4976 0.2317 0.3578 0.067 Uiso 1 1 calc R U . . .
C51 C 0.4562(5) 0.3547(5) 0.4154(4) 0.1043(16) Uani 1 1 d . . . . .
H51A H 0.4810 0.4185 0.4619 0.125 Uiso 1 1 calc R U . . .
H51B H 0.3845 0.3323 0.3763 0.125 Uiso 1 1 calc R U . . .
C52 C 0.5507(2) 0.2034(2) 0.56002(16) 0.0277(5) Uani 1 1 d . . . . .
C53 C 0.5035(2) 0.28156(19) 0.60710(16) 0.0274(5) Uani 1 1 d . . . . .
C54 C 0.5832(2) 0.3852(2) 0.65743(16) 0.0299(6) Uani 1 1 d . . . . .
H54 H 0.6690 0.4102 0.6578 0.036 Uiso 1 1 calc R U . . .
C55 C 0.5375(2) 0.4521(2) 0.70725(18) 0.0371(6) Uani 1 1 d . . . . .
H55 H 0.5923 0.5227 0.7422 0.045 Uiso 1 1 calc R U . . .
C56 C 0.4128(2) 0.4169(2) 0.70638(18) 0.0369(6) Uani 1 1 d . . . . .
H56 H 0.3820 0.4637 0.7399 0.044 Uiso 1 1 calc R U . . .
C57 C 0.3333(2) 0.3140(2) 0.65700(17) 0.0348(6) Uani 1 1 d . . . . .
H57 H 0.2476 0.2895 0.6568 0.042 Uiso 1 1 calc R U . . .
C58 C 0.3780(2) 0.2458(2) 0.60739(16) 0.0315(6) Uani 1 1 d . . . . .
H58 H 0.3229 0.1746 0.5736 0.038 Uiso 1 1 calc R U . . .
H10 H 0.899(3) -0.047(2) 0.1164(7) 0.055(9) Uiso 1 1 d D . . . .
H40 H 0.554(2) -0.0176(19) 0.3568(18) 0.056(9) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.405(3) . ?
F3 C3 1.403(3) . ?
F5 C5 1.402(3) . ?
F6 C6 1.402(3) . ?
F32 C32 1.402(3) . ?
F33 C33 1.407(3) . ?
F35 C35 1.399(3) . ?
F36 C36 1.400(3) . ?
O9 C9 1.237(3) . ?
O22 C22 1.236(3) . ?
O39 C39 1.229(3) . ?
O52 C52 1.227(3) . ?
N10 C9 1.325(3) . ?
N10 C11 1.470(3) . ?
N10 H10 0.977(5) . ?
N18 C22 1.355(3) . ?
N18 C8 1.468(3) . ?
N18 C19 1.473(3) . ?
N40 C39 1.329(3) . ?
N40 C41 1.460(3) . ?
N40 H40 0.978(5) . ?
N48 C52 1.366(3) . ?
N48 C38 1.472(3) . ?
N48 C49 1.475(3) . ?
C1 C2 1.533(3) . ?
C1 C6 1.536(3) . ?
C1 C7 1.538(3) . ?
C1 C8 1.568(3) . ?
C2 C3 1.500(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.511(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.503(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.516(3) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.537(3) . ?
C8 H8 1.0000 . ?
C11 C12 1.504(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.381(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.384(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.493(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.315(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C22 C23 1.496(3) . ?
C23 C28 1.383(3) . ?
C23 C24 1.392(3) . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C31 C32 1.534(3) . ?
C31 C37 1.539(3) . ?
C31 C36 1.541(3) . ?
C31 C38 1.574(3) . ?
C32 C33 1.511(3) . ?
C32 H32 1.0000 . ?
C33 C34 1.505(3) . ?
C33 H33 1.0000 . ?
C34 C35 1.509(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.507(3) . ?
C35 H35 1.0000 . ?
C36 H36 1.0000 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.536(3) . ?
C38 H38 1.0000 . ?
C41 C42 1.505(3) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.384(3) . ?
C42 C47 1.390(3) . ?
C43 C44 1.384(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.386(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.363(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.382(3) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C49 C50 1.496(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.356(6) . ?
C50 H50 0.9500 . ?
C51 H51A 0.9500 . ?
C51 H51B 0.9500 . ?
C52 C53 1.493(3) . ?
C53 C54 1.386(3) . ?
C53 C58 1.392(3) . ?
C54 C55 1.386(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.380(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.375(4) . ?
C56 H56 0.9500 . ?
C57 C58 1.388(4) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N10 C11 120.7(2) . . ?
C9 N10 H10 120.4(18) . . ?
C11 N10 H10 118.1(18) . . ?
C22 N18 C8 117.27(18) . . ?
C22 N18 C19 121.00(18) . . ?
C8 N18 C19 119.59(18) . . ?
C39 N40 C41 120.73(19) . . ?
C39 N40 H40 122.8(19) . . ?
C41 N40 H40 116.4(19) . . ?
C52 N48 C38 116.97(19) . . ?
C52 N48 C49 120.2(2) . . ?
C38 N48 C49 121.25(19) . . ?
C2 C1 C6 104.79(18) . . ?
C2 C1 C7 112.65(19) . . ?
C6 C1 C7 111.76(19) . . ?
C2 C1 C8 106.56(17) . . ?
C6 C1 C8 114.04(19) . . ?
C7 C1 C8 107.04(18) . . ?
F2 C2 C3 108.29(18) . . ?
F2 C2 C1 109.25(17) . . ?
C3 C2 C1 116.79(18) . . ?
F2 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C1 C2 H2 107.4 . . ?
F3 C3 C2 110.11(18) . . ?
F3 C3 C4 109.99(18) . . ?
C2 C3 C4 111.48(19) . . ?
F3 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C5 C4 C3 114.11(19) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
F5 C5 C4 109.98(19) . . ?
F5 C5 C6 109.84(19) . . ?
C4 C5 C6 112.03(18) . . ?
F5 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
C6 C5 H5 108.3 . . ?
F6 C6 C5 107.77(17) . . ?
F6 C6 C1 110.24(18) . . ?
C5 C6 C1 115.73(19) . . ?
F6 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
C1 C6 H6 107.6 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N18 C8 C9 109.08(17) . . ?
N18 C8 C1 113.77(17) . . ?
C9 C8 C1 116.08(18) . . ?
N18 C8 H8 105.7 . . ?
C9 C8 H8 105.7 . . ?
C1 C8 H8 105.7 . . ?
O9 C9 N10 122.9(2) . . ?
O9 C9 C8 122.6(2) . . ?
N10 C9 C8 114.4(2) . . ?
N10 C11 C12 109.08(19) . . ?
N10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
N10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C17 C12 C13 119.1(2) . . ?
C17 C12 C11 120.4(2) . . ?
C13 C12 C11 120.5(2) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.5(2) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
N18 C19 C20 113.2(2) . . ?
N18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
N18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 124.6(3) . . ?
C21 C20 H20 117.7 . . ?
C19 C20 H20 117.7 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
O22 C22 N18 122.7(2) . . ?
O22 C22 C23 118.6(2) . . ?
N18 C22 C23 118.7(2) . . ?
C28 C23 C24 119.0(2) . . ?
C28 C23 C22 118.6(2) . . ?
C24 C23 C22 122.0(2) . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C25 119.7(2) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 120.6(2) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
C32 C31 C37 112.1(2) . . ?
C32 C31 C36 105.51(18) . . ?
C37 C31 C36 111.9(2) . . ?
C32 C31 C38 106.07(19) . . ?
C37 C31 C38 108.03(18) . . ?
C36 C31 C38 113.11(19) . . ?
F32 C32 C33 107.94(18) . . ?
F32 C32 C31 108.85(18) . . ?
C33 C32 C31 117.4(2) . . ?
F32 C32 H32 107.4 . . ?
C33 C32 H32 107.4 . . ?
C31 C32 H32 107.4 . . ?
F33 C33 C34 109.9(2) . . ?
F33 C33 C32 110.38(19) . . ?
C34 C33 C32 111.3(2) . . ?
F33 C33 H33 108.4 . . ?
C34 C33 H33 108.4 . . ?
C32 C33 H33 108.4 . . ?
C33 C34 C35 113.4(2) . . ?
C33 C34 H34A 108.9 . . ?
C35 C34 H34A 108.9 . . ?
C33 C34 H34B 108.9 . . ?
C35 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
F35 C35 C36 110.66(19) . . ?
F35 C35 C34 109.6(2) . . ?
C36 C35 C34 111.5(2) . . ?
F35 C35 H35 108.3 . . ?
C36 C35 H35 108.3 . . ?
C34 C35 H35 108.3 . . ?
F36 C36 C35 107.90(19) . . ?
F36 C36 C31 109.54(19) . . ?
C35 C36 C31 116.2(2) . . ?
F36 C36 H36 107.6 . . ?
C35 C36 H36 107.6 . . ?
C31 C36 H36 107.6 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N48 C38 C39 110.70(19) . . ?
N48 C38 C31 113.85(19) . . ?
C39 C38 C31 113.99(18) . . ?
N48 C38 H38 105.8 . . ?
C39 C38 H38 105.8 . . ?
C31 C38 H38 105.8 . . ?
O39 C39 N40 122.3(2) . . ?
O39 C39 C38 122.2(2) . . ?
N40 C39 C38 115.50(19) . . ?
N40 C41 C42 111.91(19) . . ?
N40 C41 H41A 109.2 . . ?
C42 C41 H41A 109.2 . . ?
N40 C41 H41B 109.2 . . ?
C42 C41 H41B 109.2 . . ?
H41A C41 H41B 107.9 . . ?
C43 C42 C47 118.8(2) . . ?
C43 C42 C41 121.3(2) . . ?
C47 C42 C41 119.9(2) . . ?
C42 C43 C44 120.4(2) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C43 C44 C45 120.1(2) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C46 C45 C44 119.7(2) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C45 C46 C47 120.5(2) . . ?
C45 C46 H46 119.7 . . ?
C47 C46 H46 119.7 . . ?
C46 C47 C42 120.5(2) . . ?
C46 C47 H47 119.8 . . ?
C42 C47 H47 119.8 . . ?
N48 C49 C50 112.6(2) . . ?
N48 C49 H49A 109.1 . . ?
C50 C49 H49A 109.1 . . ?
N48 C49 H49B 109.1 . . ?
C50 C49 H49B 109.1 . . ?
H49A C49 H49B 107.8 . . ?
C51 C50 C49 121.6(4) . . ?
C51 C50 H50 119.2 . . ?
C49 C50 H50 119.2 . . ?
C50 C51 H51A 120.0 . . ?
C50 C51 H51B 120.0 . . ?
H51A C51 H51B 120.0 . . ?
O52 C52 N48 121.7(2) . . ?
O52 C52 C53 119.5(2) . . ?
N48 C52 C53 118.7(2) . . ?
C54 C53 C58 119.4(2) . . ?
C54 C53 C52 120.8(2) . . ?
C58 C53 C52 119.4(2) . . ?
C55 C54 C53 120.0(2) . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C56 C55 C54 120.4(2) . . ?
C56 C55 H55 119.8 . . ?
C54 C55 H55 119.8 . . ?
C57 C56 C55 120.0(2) . . ?
C57 C56 H56 120.0 . . ?
C55 C56 H56 120.0 . . ?
C56 C57 C58 120.2(2) . . ?
C56 C57 H57 119.9 . . ?
C58 C57 H57 119.9 . . ?
C57 C58 C53 120.1(2) . . ?
C57 C58 H58 120.0 . . ?
C53 C58 H58 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 178.18(17) . . . . ?
C7 C1 C2 F2 56.5(2) . . . . ?
C8 C1 C2 F2 -60.6(2) . . . . ?
C6 C1 C2 C3 54.9(2) . . . . ?
C7 C1 C2 C3 -66.8(3) . . . . ?
C8 C1 C2 C3 176.09(19) . . . . ?
F2 C2 C3 F3 -54.9(2) . . . . ?
C1 C2 C3 F3 68.9(2) . . . . ?
F2 C2 C3 C4 -177.24(17) . . . . ?
C1 C2 C3 C4 -53.5(3) . . . . ?
F3 C3 C4 C5 -75.4(2) . . . . ?
C2 C3 C4 C5 47.0(3) . . . . ?
C3 C4 C5 F5 75.3(2) . . . . ?
C3 C4 C5 C6 -47.2(3) . . . . ?
F5 C5 C6 F6 54.5(2) . . . . ?
C4 C5 C6 F6 177.03(19) . . . . ?
F5 C5 C6 C1 -69.4(2) . . . . ?
C4 C5 C6 C1 53.1(3) . . . . ?
C2 C1 C6 F6 -176.70(17) . . . . ?
C7 C1 C6 F6 -54.4(2) . . . . ?
C8 C1 C6 F6 67.2(2) . . . . ?
C2 C1 C6 C5 -54.1(2) . . . . ?
C7 C1 C6 C5 68.2(2) . . . . ?
C8 C1 C6 C5 -170.25(18) . . . . ?
C22 N18 C8 C9 128.3(2) . . . . ?
C19 N18 C8 C9 -35.2(3) . . . . ?
C22 N18 C8 C1 -100.3(2) . . . . ?
C19 N18 C8 C1 96.1(2) . . . . ?
C2 C1 C8 N18 179.75(18) . . . . ?
C6 C1 C8 N18 -65.2(2) . . . . ?
C7 C1 C8 N18 59.0(2) . . . . ?
C2 C1 C8 C9 -52.4(2) . . . . ?
C6 C1 C8 C9 62.7(2) . . . . ?
C7 C1 C8 C9 -173.19(19) . . . . ?
C11 N10 C9 O9 -6.1(3) . . . . ?
C11 N10 C9 C8 172.11(18) . . . . ?
N18 C8 C9 O9 92.3(2) . . . . ?
C1 C8 C9 O9 -37.8(3) . . . . ?
N18 C8 C9 N10 -86.0(2) . . . . ?
C1 C8 C9 N10 143.9(2) . . . . ?
C9 N10 C11 C12 -171.28(19) . . . . ?
N10 C11 C12 C17 99.2(2) . . . . ?
N10 C11 C12 C13 -79.3(3) . . . . ?
C17 C12 C13 C14 -0.8(4) . . . . ?
C11 C12 C13 C14 177.7(2) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C13 C12 C17 C16 0.6(3) . . . . ?
C11 C12 C17 C16 -177.8(2) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C22 N18 C19 C20 -72.7(3) . . . . ?
C8 N18 C19 C20 90.3(2) . . . . ?
N18 C19 C20 C21 -142.7(3) . . . . ?
C8 N18 C22 O22 -0.8(3) . . . . ?
C19 N18 C22 O22 162.5(2) . . . . ?
C8 N18 C22 C23 176.31(18) . . . . ?
C19 N18 C22 C23 -20.4(3) . . . . ?
O22 C22 C23 C28 -55.4(3) . . . . ?
N18 C22 C23 C28 127.4(2) . . . . ?
O22 C22 C23 C24 117.3(2) . . . . ?
N18 C22 C23 C24 -59.8(3) . . . . ?
C28 C23 C24 C25 0.5(3) . . . . ?
C22 C23 C24 C25 -172.2(2) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C27 -1.0(4) . . . . ?
C25 C26 C27 C28 1.3(4) . . . . ?
C26 C27 C28 C23 -0.7(4) . . . . ?
C24 C23 C28 C27 -0.2(3) . . . . ?
C22 C23 C28 C27 172.7(2) . . . . ?
C37 C31 C32 F32 52.1(2) . . . . ?
C36 C31 C32 F32 174.13(19) . . . . ?
C38 C31 C32 F32 -65.6(2) . . . . ?
C37 C31 C32 C33 -70.9(3) . . . . ?
C36 C31 C32 C33 51.2(3) . . . . ?
C38 C31 C32 C33 171.44(19) . . . . ?
F32 C32 C33 F33 -53.2(2) . . . . ?
C31 C32 C33 F33 70.2(3) . . . . ?
F32 C32 C33 C34 -175.52(19) . . . . ?
C31 C32 C33 C34 -52.1(3) . . . . ?
F33 C33 C34 C35 -73.3(3) . . . . ?
C32 C33 C34 C35 49.3(3) . . . . ?
C33 C34 C35 F35 72.1(3) . . . . ?
C33 C34 C35 C36 -50.8(3) . . . . ?
F35 C35 C36 F36 55.5(2) . . . . ?
C34 C35 C36 F36 177.69(19) . . . . ?
F35 C35 C36 C31 -67.9(3) . . . . ?
C34 C35 C36 C31 54.3(3) . . . . ?
C32 C31 C36 F36 -174.55(18) . . . . ?
C37 C31 C36 F36 -52.4(3) . . . . ?
C38 C31 C36 F36 69.9(2) . . . . ?
C32 C31 C36 C35 -52.0(3) . . . . ?
C37 C31 C36 C35 70.2(3) . . . . ?
C38 C31 C36 C35 -167.5(2) . . . . ?
C52 N48 C38 C39 128.9(2) . . . . ?
C49 N48 C38 C39 -36.6(3) . . . . ?
C52 N48 C38 C31 -101.1(2) . . . . ?
C49 N48 C38 C31 93.4(2) . . . . ?
C32 C31 C38 N48 174.86(18) . . . . ?
C37 C31 C38 N48 54.5(2) . . . . ?
C36 C31 C38 N48 -70.0(2) . . . . ?
C32 C31 C38 C39 -56.8(2) . . . . ?
C37 C31 C38 C39 -177.22(19) . . . . ?
C36 C31 C38 C39 58.3(3) . . . . ?
C41 N40 C39 O39 -1.0(3) . . . . ?
C41 N40 C39 C38 179.0(2) . . . . ?
N48 C38 C39 O39 70.5(3) . . . . ?
C31 C38 C39 O39 -59.3(3) . . . . ?
N48 C38 C39 N40 -109.5(2) . . . . ?
C31 C38 C39 N40 120.6(2) . . . . ?
C39 N40 C41 C42 -156.3(2) . . . . ?
N40 C41 C42 C43 -73.0(3) . . . . ?
N40 C41 C42 C47 108.3(3) . . . . ?
C47 C42 C43 C44 0.1(4) . . . . ?
C41 C42 C43 C44 -178.5(2) . . . . ?
C42 C43 C44 C45 0.4(4) . . . . ?
C43 C44 C45 C46 -0.7(4) . . . . ?
C44 C45 C46 C47 0.3(4) . . . . ?
C45 C46 C47 C42 0.2(4) . . . . ?
C43 C42 C47 C46 -0.4(4) . . . . ?
C41 C42 C47 C46 178.3(2) . . . . ?
C52 N48 C49 C50 -67.3(3) . . . . ?
C38 N48 C49 C50 97.8(3) . . . . ?
N48 C49 C50 C51 123.9(4) . . . . ?
C38 N48 C52 O52 -5.7(3) . . . . ?
C49 N48 C52 O52 159.9(2) . . . . ?
C38 N48 C52 C53 171.2(2) . . . . ?
C49 N48 C52 C53 -23.2(3) . . . . ?
O52 C52 C53 C54 120.2(3) . . . . ?
N48 C52 C53 C54 -56.8(3) . . . . ?
O52 C52 C53 C58 -53.4(3) . . . . ?
N48 C52 C53 C58 129.6(2) . . . . ?
C58 C53 C54 C55 -0.2(4) . . . . ?
C52 C53 C54 C55 -173.7(2) . . . . ?
C53 C54 C55 C56 -0.8(4) . . . . ?
C54 C55 C56 C57 1.1(4) . . . . ?
C55 C56 C57 C58 -0.6(4) . . . . ?
C56 C57 C58 C53 -0.3(4) . . . . ?
C54 C53 C58 C57 0.7(4) . . . . ?
C52 C53 C58 C57 174.3(2) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20
_database_code_depnum_ccdc_archive 'CCDC 1436758'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-21
_audit_creation_method           'by CrystalStructure 4.1'



_chemical_formula_sum            'C20 H25 F4 N O3'
_chemical_formula_moiety         'C20 H25 F4 N O3'
_chemical_formula_weight         403.42
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.0424(16)
_cell_length_b                   10.270(2)
_cell_length_c                   10.882(2)
_cell_angle_alpha                83.19(3)
_cell_angle_beta                 64.29(2)
_cell_angle_gamma                74.10(2)
_cell_volume                     972.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2474
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424.00
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.327
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            14251
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_min         2.062
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3530
_reflns_number_gt                2720
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1081
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3530
_refine_ls_number_parameters     261
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.20267(11) 0.56011(10) -0.01358(9) 0.0345(3) Uani 1 1 d . . . . .
F3 F 0.46595(10) 0.36564(10) -0.13134(10) 0.0350(3) Uani 1 1 d . . . . .
F5 F 0.48655(10) 0.14626(10) 0.05230(10) 0.0355(3) Uani 1 1 d . . . . .
F6 F 0.22898(11) 0.19534(9) 0.29615(10) 0.0352(3) Uani 1 1 d . . . . .
O9 O -0.09130(12) 0.66232(12) 0.20760(12) 0.0305(3) Uani 1 1 d . . . . .
O15 O -0.06506(11) 0.40354(11) 0.27948(11) 0.0254(3) Uani 1 1 d . . . . .
O16 O -0.19443(12) 0.45596(12) 0.50221(11) 0.0290(3) Uani 1 1 d . . . . .
N10 N 0.06601(14) 0.68895(13) 0.29874(14) 0.0258(3) Uani 1 1 d D . . . .
C1 C 0.20514(16) 0.38966(16) 0.15491(16) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.19887(17) 0.42516(16) 0.01581(16) 0.0260(4) Uani 1 1 d . . . . .
H2 H 0.0991 0.4153 0.0237 0.031 Uiso 1 1 calc R U . . .
C3 C 0.32499(17) 0.33974(18) -0.10361(17) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.3029 0.3648 -0.1857 0.034 Uiso 1 1 calc R U . . .
C4 C 0.33565(18) 0.19027(18) -0.07612(17) 0.0308(4) Uani 1 1 d . . . . .
H4A H 0.4278 0.1380 -0.1505 0.037 Uiso 1 1 calc R U . . .
H4B H 0.2457 0.1690 -0.0769 0.037 Uiso 1 1 calc R U . . .
C5 C 0.34321(18) 0.14569(18) 0.05906(18) 0.0302(4) Uani 1 1 d . . . . .
H5 H 0.3302 0.0512 0.0783 0.036 Uiso 1 1 calc R U . . .
C6 C 0.21676(18) 0.23649(16) 0.17306(16) 0.0263(4) Uani 1 1 d . . . . .
H6 H 0.1182 0.2223 0.1823 0.032 Uiso 1 1 calc R U . . .
C7 C 0.33826(17) 0.42895(17) 0.16407(17) 0.0264(4) Uani 1 1 d . . . . .
H7A H 0.3317 0.5253 0.1425 0.032 Uiso 1 1 calc R U . . .
H7B H 0.4354 0.3748 0.0989 0.032 Uiso 1 1 calc R U . . .
H7C H 0.3322 0.4118 0.2567 0.032 Uiso 1 1 calc R U . . .
C8 C 0.05379(17) 0.46190(16) 0.27283(17) 0.0245(4) Uani 1 1 d . . . . .
H8 H 0.0650 0.4433 0.3606 0.029 Uiso 1 1 calc R U . . .
C9 C 0.00166(17) 0.61610(17) 0.25641(16) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.04540(18) 0.83790(17) 0.28316(17) 0.0280(4) Uani 1 1 d . . . . .
C12 C -0.12146(18) 0.91003(18) 0.36405(19) 0.0325(4) Uani 1 1 d . . . . .
H12A H -0.1548 0.8805 0.4594 0.039 Uiso 1 1 calc R U . . .
H12B H -0.1843 0.8878 0.3253 0.039 Uiso 1 1 calc R U . . .
H12C H -0.1326 1.0081 0.3594 0.039 Uiso 1 1 calc R U . . .
C13 C 0.1449(2) 0.87357(18) 0.3414(2) 0.0347(4) Uani 1 1 d . . . . .
H13A H 0.2514 0.8245 0.2909 0.042 Uiso 1 1 calc R U . . .
H13B H 0.1104 0.8479 0.4378 0.042 Uiso 1 1 calc R U . . .
H13C H 0.1367 0.9712 0.3327 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0991(2) 0.87451(19) 0.13249(18) 0.0365(4) Uani 1 1 d . . . . .
H14A H 0.0406 0.8435 0.0946 0.044 Uiso 1 1 calc R U . . .
H14B H 0.2078 0.8307 0.0838 0.044 Uiso 1 1 calc R U . . .
H14C H 0.0834 0.9729 0.1221 0.044 Uiso 1 1 calc R U . . .
C16 C -0.18378(17) 0.40507(16) 0.40216(17) 0.0244(4) Uani 1 1 d . . . . .
C17 C -0.29348(16) 0.33554(16) 0.39870(16) 0.0242(4) Uani 1 1 d . . . . .
C18 C -0.27197(18) 0.27687(17) 0.28033(17) 0.0266(4) Uani 1 1 d . . . . .
H18 H -0.1856 0.2824 0.1977 0.032 Uiso 1 1 calc R U . . .
C19 C -0.37575(18) 0.21052(18) 0.28231(18) 0.0305(4) Uani 1 1 d . . . . .
H19 H -0.3607 0.1710 0.2012 0.037 Uiso 1 1 calc R U . . .
C20 C -0.50141(18) 0.20179(19) 0.40265(19) 0.0344(4) Uani 1 1 d . . . . .
H20 H -0.5718 0.1551 0.4045 0.041 Uiso 1 1 calc R U . . .
C21 C -0.52446(19) 0.26116(19) 0.52040(18) 0.0357(4) Uani 1 1 d . . . . .
H21 H -0.6116 0.2561 0.6025 0.043 Uiso 1 1 calc R U . . .
C22 C -0.42155(18) 0.32780(18) 0.51927(18) 0.0304(4) Uani 1 1 d . . . . .
H22 H -0.4379 0.3682 0.6004 0.036 Uiso 1 1 calc R U . . .
H10 H 0.1276(18) 0.6411(17) 0.3464(17) 0.045(5) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.3921(18) . ?
F3 C3 1.4079(17) . ?
F5 C5 1.4107(17) . ?
F6 C6 1.4028(18) . ?
O9 C9 1.2274(19) . ?
O15 C16 1.3482(19) . ?
O15 C8 1.4477(17) . ?
O16 C16 1.214(2) . ?
N10 C9 1.340(2) . ?
N10 C11 1.486(2) . ?
N10 H10 0.972(5) . ?
C1 C2 1.539(2) . ?
C1 C6 1.540(2) . ?
C1 C7 1.543(2) . ?
C1 C8 1.557(2) . ?
C2 C3 1.515(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.512(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.510(2) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.541(2) . ?
C8 H8 1.0000 . ?
C11 C14 1.523(2) . ?
C11 C12 1.525(2) . ?
C11 C13 1.529(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.483(2) . ?
C17 C18 1.393(2) . ?
C17 C22 1.396(2) . ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O15 C8 116.72(12) . . ?
C9 N10 C11 124.97(14) . . ?
C9 N10 H10 117.4(11) . . ?
C11 N10 H10 117.6(11) . . ?
C2 C1 C6 105.46(13) . . ?
C2 C1 C7 112.55(12) . . ?
C6 C1 C7 112.56(13) . . ?
C2 C1 C8 110.93(13) . . ?
C6 C1 C8 106.96(12) . . ?
C7 C1 C8 108.26(12) . . ?
F2 C2 C3 108.16(13) . . ?
F2 C2 C1 108.73(13) . . ?
C3 C2 C1 115.78(14) . . ?
F2 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C1 C2 H2 108.0 . . ?
F3 C3 C4 109.21(13) . . ?
F3 C3 C2 110.02(13) . . ?
C4 C3 C2 111.63(14) . . ?
F3 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C3 C4 C5 113.11(14) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
F5 C5 C6 110.33(13) . . ?
F5 C5 C4 110.23(13) . . ?
C6 C5 C4 110.62(14) . . ?
F5 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C4 C5 H5 108.5 . . ?
F6 C6 C5 109.42(13) . . ?
F6 C6 C1 108.79(13) . . ?
C5 C6 C1 116.80(14) . . ?
F6 C6 H6 107.1 . . ?
C5 C6 H6 107.1 . . ?
C1 C6 H6 107.1 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O15 C8 C9 107.40(12) . . ?
O15 C8 C1 107.36(12) . . ?
C9 C8 C1 115.36(13) . . ?
O15 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C1 C8 H8 108.9 . . ?
O9 C9 N10 125.58(15) . . ?
O9 C9 C8 120.00(14) . . ?
N10 C9 C8 114.42(14) . . ?
N10 C11 C14 109.33(14) . . ?
N10 C11 C12 110.02(13) . . ?
C14 C11 C12 111.16(14) . . ?
N10 C11 C13 105.87(13) . . ?
C14 C11 C13 110.38(14) . . ?
C12 C11 C13 109.95(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O16 C16 O15 122.44(14) . . ?
O16 C16 C17 125.55(14) . . ?
O15 C16 C17 112.00(14) . . ?
C18 C17 C22 119.32(14) . . ?
C18 C17 C16 122.32(14) . . ?
C22 C17 C16 118.35(15) . . ?
C19 C18 C17 120.41(15) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.92(16) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.00(15) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.45(16) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 119.88(16) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 -174.49(11) . . . . ?
C7 C1 C2 F2 -51.40(16) . . . . ?
C8 C1 C2 F2 70.06(15) . . . . ?
C6 C1 C2 C3 -52.52(16) . . . . ?
C7 C1 C2 C3 70.56(17) . . . . ?
C8 C1 C2 C3 -167.98(13) . . . . ?
F2 C2 C3 F3 54.84(17) . . . . ?
C1 C2 C3 F3 -67.43(17) . . . . ?
F2 C2 C3 C4 176.26(12) . . . . ?
C1 C2 C3 C4 53.99(18) . . . . ?
F3 C3 C4 C5 71.06(16) . . . . ?
C2 C3 C4 C5 -50.83(18) . . . . ?
C3 C4 C5 F5 -71.81(17) . . . . ?
C3 C4 C5 C6 50.48(17) . . . . ?
F5 C5 C6 F6 -56.15(17) . . . . ?
C4 C5 C6 F6 -178.38(12) . . . . ?
F5 C5 C6 C1 67.95(18) . . . . ?
C4 C5 C6 C1 -54.28(18) . . . . ?
C2 C1 C6 F6 177.74(11) . . . . ?
C7 C1 C6 F6 54.66(16) . . . . ?
C8 C1 C6 F6 -64.11(15) . . . . ?
C2 C1 C6 C5 53.32(17) . . . . ?
C7 C1 C6 C5 -69.75(18) . . . . ?
C8 C1 C6 C5 171.47(13) . . . . ?
C16 O15 C8 C9 -83.19(16) . . . . ?
C16 O15 C8 C1 152.18(13) . . . . ?
C2 C1 C8 O15 67.24(15) . . . . ?
C6 C1 C8 O15 -47.28(16) . . . . ?
C7 C1 C8 O15 -168.81(12) . . . . ?
C2 C1 C8 C9 -52.42(17) . . . . ?
C6 C1 C8 C9 -166.94(13) . . . . ?
C7 C1 C8 C9 71.53(17) . . . . ?
C11 N10 C9 O9 -5.4(3) . . . . ?
C11 N10 C9 C8 174.49(13) . . . . ?
O15 C8 C9 O9 -23.92(19) . . . . ?
C1 C8 C9 O9 95.73(17) . . . . ?
O15 C8 C9 N10 156.22(13) . . . . ?
C1 C8 C9 N10 -84.14(17) . . . . ?
C9 N10 C11 C14 -58.99(19) . . . . ?
C9 N10 C11 C12 63.3(2) . . . . ?
C9 N10 C11 C13 -177.90(15) . . . . ?
C8 O15 C16 O16 2.1(2) . . . . ?
C8 O15 C16 C17 -176.56(12) . . . . ?
O16 C16 C17 C18 -178.60(15) . . . . ?
O15 C16 C17 C18 0.0(2) . . . . ?
O16 C16 C17 C22 0.6(2) . . . . ?
O15 C16 C17 C22 179.24(14) . . . . ?
C22 C17 C18 C19 -0.6(2) . . . . ?
C16 C17 C18 C19 178.68(14) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C17 0.1(3) . . . . ?
C18 C17 C22 C21 0.7(2) . . . . ?
C16 C17 C22 C21 -178.61(15) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_25
_database_code_depnum_ccdc_archive 'CCDC 1436759'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-21
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C21 H23 F4 N2 O2'
_chemical_formula_moiety         'C21 H23 F4 N2 O2'
_chemical_formula_weight         411.42
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.5702(17)
_cell_length_b                   21.691(4)
_cell_length_c                   11.256(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.986(4)
_cell_angle_gamma                90.0000
_cell_volume                     2092.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5369
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860.00
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_T_max  0.989

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            15420
_diffrn_reflns_av_R_equivalents  0.1122
_diffrn_reflns_theta_max         25.417
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3841
_reflns_number_gt                2833
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2041
_refine_ls_wR_factor_gt          0.1929
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3841
_refine_ls_number_parameters     267
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1143P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.81
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.27178(19) 0.58926(7) 0.33820(14) 0.0328(4) Uani 1 1 d . . . . .
F2 F 0.12358(18) 0.64560(7) 0.52497(14) 0.0355(4) Uani 1 1 d . . . . .
F3 F -0.0069(2) 0.75075(8) 0.44888(16) 0.0452(5) Uani 1 1 d . . . . .
F5 F 0.27404(19) 0.65653(7) 0.13469(14) 0.0353(4) Uani 1 1 d . . . . .
O9 O 0.3936(2) 0.67414(8) 0.73115(17) 0.0350(5) Uani 1 1 d . . . . .
O22 O 0.5843(2) 0.53637(8) 0.40232(17) 0.0322(5) Uani 1 1 d . . . . .
N10 N 0.3462(3) 0.57149(10) 0.7242(2) 0.0299(6) Uani 1 1 d D . . . .
N18 N 0.6150(3) 0.60964(10) 0.5445(2) 0.0295(5) Uani 1 1 d . . . . .
C1 C 0.3829(3) 0.67110(11) 0.4598(2) 0.0287(6) Uani 1 1 d . . . . .
C2 C 0.2227(3) 0.69565(12) 0.4998(3) 0.0315(6) Uani 1 1 d . . . . .
H2 H 0.2384 0.7205 0.5739 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1423(3) 0.73591(13) 0.4062(3) 0.0347(7) Uani 1 1 d . . . . .
H3 H 0.2037 0.7747 0.3963 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1240(3) 0.70423(13) 0.2865(3) 0.0339(7) Uani 1 1 d . . . . .
H4A H 0.0750 0.7326 0.2279 0.041 Uiso 1 1 calc R U . . .
H4B H 0.0571 0.6673 0.2936 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2866(3) 0.68582(12) 0.2464(2) 0.0310(6) Uani 1 1 d . . . . .
H5 H 0.3517 0.7238 0.2384 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3659(3) 0.64250(11) 0.3337(2) 0.0296(6) Uani 1 1 d . . . . .
H6 H 0.4714 0.6312 0.3039 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4981(3) 0.72659(12) 0.4560(3) 0.0340(7) Uani 1 1 d . . . . .
C8 C 0.4427(3) 0.61856(12) 0.5463(2) 0.0288(6) Uani 1 1 d . . . . .
H8 H 0.3956 0.5793 0.5159 0.035 Uiso 1 1 calc R U . . .
C9 C 0.3915(3) 0.62472(12) 0.6768(2) 0.0295(6) Uani 1 1 d . . . . .
C11 C 0.3097(4) 0.56564(12) 0.8508(3) 0.0348(7) Uani 1 1 d . . . . .
H11A H 0.2209 0.5928 0.8702 0.042 Uiso 1 1 calc R U . . .
H11B H 0.4010 0.5784 0.9001 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2685(3) 0.49944(13) 0.8774(2) 0.0311(7) Uani 1 1 d . . . . .
C13 C 0.1133(4) 0.48065(14) 0.8796(3) 0.0391(7) Uani 1 1 d . . . . .
H13 H 0.0327 0.5101 0.8666 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0746(4) 0.41926(15) 0.9008(3) 0.0472(9) Uani 1 1 d . . . . .
H14 H -0.0319 0.4071 0.9029 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1914(4) 0.37597(14) 0.9188(3) 0.0432(8) Uani 1 1 d . . . . .
H15 H 0.1654 0.3341 0.9333 0.052 Uiso 1 1 calc R U . . .
C16 C 0.3464(4) 0.39401(13) 0.9154(3) 0.0393(7) Uani 1 1 d . . . . .
H16 H 0.4267 0.3643 0.9272 0.047 Uiso 1 1 calc R U . . .
C17 C 0.3849(3) 0.45506(13) 0.8949(3) 0.0341(7) Uani 1 1 d . . . . .
H17 H 0.4915 0.4669 0.8928 0.041 Uiso 1 1 calc R U . . .
C19 C 0.7169(3) 0.64448(12) 0.6279(3) 0.0337(7) Uani 1 1 d . . . . .
H19A H 0.6652 0.6841 0.6463 0.040 Uiso 1 1 calc R U . . .
H19B H 0.8154 0.6542 0.5872 0.040 Uiso 1 1 calc R U . . .
C20 C 0.7565(3) 0.61241(13) 0.7433(3) 0.0357(7) Uani 1 1 d . . . . .
H20 H 0.8096 0.6363 0.8021 0.043 Uiso 1 1 calc R U . . .
C21 C 0.7255(3) 0.55486(13) 0.7715(3) 0.0366(7) Uani 1 1 d . . . . .
H21A H 0.6726 0.5289 0.7160 0.044 Uiso 1 1 calc R U . . .
H21B H 0.7560 0.5393 0.8473 0.044 Uiso 1 1 calc R U . . .
C22 C 0.6719(3) 0.56500(12) 0.4714(3) 0.0302(7) Uani 1 1 d . . . . .
C23 C 0.8446(4) 0.55187(14) 0.4747(3) 0.0419(8) Uani 1 1 d . . . . .
H23A H 0.8987 0.5822 0.4258 0.050 Uiso 1 1 calc R U . . .
H23B H 0.8635 0.5104 0.4435 0.050 Uiso 1 1 calc R U . . .
H23C H 0.8838 0.5544 0.5568 0.050 Uiso 1 1 calc R U . . .
H10 H 0.361(4) 0.5328(8) 0.681(3) 0.046(9) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.410(3) . ?
F2 C2 1.410(3) . ?
F3 C3 1.411(3) . ?
F5 C5 1.412(3) . ?
O9 C9 1.234(3) . ?
O22 C22 1.239(3) . ?
N10 C9 1.332(3) . ?
N10 C11 1.470(4) . ?
N10 H10 0.979(5) . ?
N18 C22 1.366(4) . ?
N18 C19 1.478(4) . ?
N18 C8 1.490(4) . ?
C1 C2 1.547(4) . ?
C1 C6 1.553(4) . ?
C1 C7 1.558(4) . ?
C1 C8 1.579(4) . ?
C2 C3 1.524(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.519(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.525(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.513(4) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C8 C9 1.546(4) . ?
C8 H8 1.0000 . ?
C11 C12 1.510(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.392(4) . ?
C12 C17 1.398(4) . ?
C13 C14 1.394(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.508(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.316(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C22 C23 1.506(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N10 C11 122.1(2) . . ?
C9 N10 H10 120.3(19) . . ?
C11 N10 H10 115.9(19) . . ?
C22 N18 C19 122.1(2) . . ?
C22 N18 C8 117.7(2) . . ?
C19 N18 C8 120.0(2) . . ?
C2 C1 C6 109.5(2) . . ?
C2 C1 C7 107.9(2) . . ?
C6 C1 C7 109.5(2) . . ?
C2 C1 C8 110.4(2) . . ?
C6 C1 C8 107.4(2) . . ?
C7 C1 C8 112.0(2) . . ?
F2 C2 C3 108.3(2) . . ?
F2 C2 C1 109.5(2) . . ?
C3 C2 C1 112.9(2) . . ?
F2 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
F3 C3 C4 109.0(2) . . ?
F3 C3 C2 107.3(2) . . ?
C4 C3 C2 113.1(2) . . ?
F3 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C3 C4 C5 107.5(2) . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
F5 C5 C6 109.0(2) . . ?
F5 C5 C4 109.0(2) . . ?
C6 C5 C4 111.9(2) . . ?
F5 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
C4 C5 H5 109.0 . . ?
F1 C6 C5 106.3(2) . . ?
F1 C6 C1 109.8(2) . . ?
C5 C6 C1 112.3(2) . . ?
F1 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C1 C6 H6 109.4 . . ?
N18 C8 C9 108.7(2) . . ?
N18 C8 C1 113.4(2) . . ?
C9 C8 C1 115.4(2) . . ?
N18 C8 H8 106.2 . . ?
C9 C8 H8 106.2 . . ?
C1 C8 H8 106.2 . . ?
O9 C9 N10 123.8(3) . . ?
O9 C9 C8 123.0(2) . . ?
N10 C9 C8 113.3(2) . . ?
N10 C11 C12 109.2(2) . . ?
N10 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
N10 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C17 118.4(3) . . ?
C13 C12 C11 120.6(3) . . ?
C17 C12 C11 121.0(3) . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 120.7(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N18 C19 C20 115.7(2) . . ?
N18 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
N18 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C19 127.0(3) . . ?
C21 C20 H20 116.5 . . ?
C19 C20 H20 116.5 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
O22 C22 N18 121.0(3) . . ?
O22 C22 C23 120.3(2) . . ?
N18 C22 C23 118.7(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 71.4(3) . . . . ?
C7 C1 C2 F2 -169.4(2) . . . . ?
C8 C1 C2 F2 -46.7(3) . . . . ?
C6 C1 C2 C3 -49.3(3) . . . . ?
C7 C1 C2 C3 69.8(3) . . . . ?
C8 C1 C2 C3 -167.4(2) . . . . ?
F2 C2 C3 F3 53.6(3) . . . . ?
C1 C2 C3 F3 175.0(2) . . . . ?
F2 C2 C3 C4 -66.6(3) . . . . ?
C1 C2 C3 C4 54.8(3) . . . . ?
F3 C3 C4 C5 -177.0(2) . . . . ?
C2 C3 C4 C5 -57.8(3) . . . . ?
C3 C4 C5 F5 -179.6(2) . . . . ?
C3 C4 C5 C6 59.7(3) . . . . ?
F5 C5 C6 F1 -59.3(2) . . . . ?
C4 C5 C6 F1 61.3(3) . . . . ?
F5 C5 C6 C1 -179.4(2) . . . . ?
C4 C5 C6 C1 -58.8(3) . . . . ?
C2 C1 C6 F1 -66.5(3) . . . . ?
C7 C1 C6 F1 175.3(2) . . . . ?
C8 C1 C6 F1 53.4(3) . . . . ?
C2 C1 C6 C5 51.5(3) . . . . ?
C7 C1 C6 C5 -66.6(3) . . . . ?
C8 C1 C6 C5 171.5(2) . . . . ?
C22 N18 C8 C9 135.1(2) . . . . ?
C19 N18 C8 C9 -39.4(3) . . . . ?
C22 N18 C8 C1 -95.0(3) . . . . ?
C19 N18 C8 C1 90.4(3) . . . . ?
C2 C1 C8 N18 -157.6(2) . . . . ?
C6 C1 C8 N18 83.1(3) . . . . ?
C7 C1 C8 N18 -37.2(3) . . . . ?
C2 C1 C8 C9 -31.2(3) . . . . ?
C6 C1 C8 C9 -150.6(2) . . . . ?
C7 C1 C8 C9 89.2(3) . . . . ?
C11 N10 C9 O9 -6.6(4) . . . . ?
C11 N10 C9 C8 173.0(2) . . . . ?
N18 C8 C9 O9 85.6(3) . . . . ?
C1 C8 C9 O9 -43.1(4) . . . . ?
N18 C8 C9 N10 -94.1(3) . . . . ?
C1 C8 C9 N10 137.2(3) . . . . ?
C9 N10 C11 C12 -177.8(3) . . . . ?
N10 C11 C12 C13 -96.7(3) . . . . ?
N10 C11 C12 C17 80.4(3) . . . . ?
C17 C12 C13 C14 1.0(4) . . . . ?
C11 C12 C13 C14 178.2(3) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?
C13 C12 C17 C16 -0.7(4) . . . . ?
C11 C12 C17 C16 -177.9(3) . . . . ?
C22 N18 C19 C20 -81.3(3) . . . . ?
C8 N18 C19 C20 93.0(3) . . . . ?
N18 C19 C20 C21 8.5(4) . . . . ?
C19 N18 C22 O22 180.0(2) . . . . ?
C8 N18 C22 O22 5.6(4) . . . . ?
C19 N18 C22 C23 -1.2(4) . . . . ?
C8 N18 C22 C23 -175.6(2) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_26
_database_code_depnum_ccdc_archive 'CCDC 1436760'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-23
_audit_creation_method           'by CrystalStructure 4.1'



_chemical_formula_sum            'C26 H28 F4 N2 O2'
_chemical_formula_moiety         'C26 H28 F4 N2 O2'
_chemical_formula_weight         476.51
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.187(6)
_cell_length_b                   11.294(5)
_cell_length_c                   12.180(6)
_cell_angle_alpha                92.707(4)
_cell_angle_beta                 116.606(5)
_cell_angle_gamma                116.789(5)
_cell_volume                     1166.9(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1530
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      27.30
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             500.00
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_T_max  0.999

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            12356
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_theta_max         25.312
_diffrn_reflns_theta_min         1.968
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4208
_reflns_number_gt                2385
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1364
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4208
_refine_ls_number_parameters     312
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1043P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.86
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 1.09420(19) 0.33089(18) 0.83806(15) 0.0321(5) Uani 1 1 d . . . . .
F3 F 1.0282(2) 0.17752(19) 0.98698(16) 0.0387(5) Uani 1 1 d . . . . .
F5 F 0.6169(2) -0.05834(18) 0.54822(15) 0.0354(5) Uani 1 1 d . . . . .
F6 F 0.8634(2) 0.18412(18) 0.58891(15) 0.0313(4) Uani 1 1 d . . . . .
O9 O 1.0514(3) 0.6150(2) 0.90312(19) 0.0380(6) Uani 1 1 d . . . . .
O22 O 0.8418(2) 0.3754(2) 0.44384(18) 0.0313(5) Uani 1 1 d . . . . .
N10 N 1.1829(3) 0.6628(3) 0.7994(2) 0.0275(6) Uani 1 1 d D . . . .
N18 N 0.8179(3) 0.4737(3) 0.5934(2) 0.0253(6) Uani 1 1 d . . . . .
C1 C 0.8486(3) 0.3210(3) 0.7351(3) 0.0263(7) Uani 1 1 d . . . . .
C2 C 0.9725(3) 0.3148(3) 0.8554(3) 0.0277(7) Uani 1 1 d . . . . .
H2 H 1.0175 0.3933 0.9315 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9057(4) 0.1792(3) 0.8836(3) 0.0299(7) Uani 1 1 d . . . . .
H3 H 0.8304 0.1740 0.9090 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8206(4) 0.0517(3) 0.7704(3) 0.0305(7) Uani 1 1 d . . . . .
H4A H 0.7735 -0.0341 0.7926 0.037 Uiso 1 1 calc R U . . .
H4B H 0.8954 0.0502 0.7488 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6931(4) 0.0573(3) 0.6564(3) 0.0300(7) Uani 1 1 d . . . . .
H5 H 0.6149 0.0535 0.6773 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7605(3) 0.1885(3) 0.6215(3) 0.0261(7) Uani 1 1 d . . . . .
H6 H 0.6736 0.1883 0.5450 0.031 Uiso 1 1 calc R U . . .
C7 C 0.7303(4) 0.3269(3) 0.7622(3) 0.0291(7) Uani 1 1 d . . . . .
H7A H 0.6455 0.3219 0.6829 0.035 Uiso 1 1 calc R U . . .
H7B H 0.7835 0.4146 0.8294 0.035 Uiso 1 1 calc R U . . .
H7C H 0.6858 0.2480 0.7917 0.035 Uiso 1 1 calc R U . . .
C8 C 0.9319(3) 0.4494(3) 0.6964(3) 0.0247(7) Uani 1 1 d . . . . .
H8 H 0.9853 0.4262 0.6594 0.030 Uiso 1 1 calc R U . . .
C9 C 1.0605(4) 0.5850(3) 0.8105(3) 0.0267(7) Uani 1 1 d . . . . .
C11 C 1.3163(4) 0.7987(3) 0.8930(3) 0.0329(8) Uani 1 1 d . . . . .
H11A H 1.4147 0.8096 0.9049 0.040 Uiso 1 1 calc R U . . .
H11B H 1.3238 0.8033 0.9774 0.040 Uiso 1 1 calc R U . . .
C12 C 1.3003(4) 0.9161(3) 0.8500(3) 0.0323(8) Uani 1 1 d . . . . .
C13 C 1.2605(4) 0.9898(4) 0.9053(3) 0.0359(8) Uani 1 1 d . . . . .
H13 H 1.2522 0.9722 0.9779 0.043 Uiso 1 1 calc R U . . .
C14 C 1.2324(4) 1.0890(4) 0.8572(3) 0.0458(9) Uani 1 1 d . . . . .
H14 H 1.2050 1.1390 0.8964 0.055 Uiso 1 1 calc R U . . .
C15 C 1.2443(6) 1.1147(4) 0.7524(4) 0.0672(14) Uani 1 1 d . . . . .
H15 H 1.2231 1.1813 0.7176 0.081 Uiso 1 1 calc R U . . .
C16 C 1.2868(6) 1.0440(5) 0.6983(4) 0.0730(15) Uani 1 1 d . . . . .
H16 H 1.2962 1.0629 0.6264 0.088 Uiso 1 1 calc R U . . .
C17 C 1.3160(5) 0.9462(4) 0.7461(3) 0.0517(11) Uani 1 1 d . . . . .
H17 H 1.3470 0.8991 0.7083 0.062 Uiso 1 1 calc R U . . .
C19 C 0.7710(4) 0.5662(3) 0.6266(3) 0.0302(7) Uani 1 1 d . . . . .
H19A H 0.7922 0.5739 0.7156 0.036 Uiso 1 1 calc R U . . .
H19B H 0.6562 0.5230 0.5675 0.036 Uiso 1 1 calc R U . . .
C20 C 0.8539(4) 0.7090(4) 0.6187(3) 0.0365(8) Uani 1 1 d . . . . .
H20 H 0.9657 0.7609 0.6697 0.044 Uiso 1 1 calc R U . . .
C21 C 0.7888(5) 0.7675(4) 0.5502(4) 0.0524(10) Uani 1 1 d . . . . .
H21A H 0.6773 0.7195 0.4977 0.063 Uiso 1 1 calc R U . . .
H21B H 0.8515 0.8593 0.5513 0.063 Uiso 1 1 calc R U . . .
C22 C 0.7811(3) 0.4298(3) 0.4708(3) 0.0248(7) Uani 1 1 d . . . . .
C23 C 0.6524(4) 0.4380(3) 0.3623(3) 0.0256(7) Uani 1 1 d . . . . .
C24 C 0.6854(4) 0.5211(3) 0.2877(3) 0.0297(7) Uani 1 1 d . . . . .
H24 H 0.7914 0.5830 0.3117 0.036 Uiso 1 1 calc R U . . .
C25 C 0.5639(4) 0.5137(4) 0.1784(3) 0.0344(8) Uani 1 1 d . . . . .
H25 H 0.5864 0.5720 0.1278 0.041 Uiso 1 1 calc R U . . .
C26 C 0.4101(4) 0.4225(4) 0.1418(3) 0.0353(8) Uani 1 1 d . . . . .
H26 H 0.3267 0.4163 0.0651 0.042 Uiso 1 1 calc R U . . .
C27 C 0.3767(4) 0.3402(4) 0.2161(3) 0.0333(8) Uani 1 1 d . . . . .
H27 H 0.2705 0.2781 0.1914 0.040 Uiso 1 1 calc R U . . .
C28 C 0.4981(4) 0.3484(3) 0.3267(3) 0.0290(7) Uani 1 1 d . . . . .
H28 H 0.4754 0.2921 0.3785 0.035 Uiso 1 1 calc R U . . .
H10 H 1.176(4) 0.637(3) 0.7182(16) 0.035(9) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.404(4) . ?
F3 C3 1.395(3) . ?
F5 C5 1.413(3) . ?
F6 C6 1.394(3) . ?
O9 C9 1.223(4) . ?
O22 C22 1.226(4) . ?
N10 C9 1.326(4) . ?
N10 C11 1.459(4) . ?
N10 H10 0.977(5) . ?
N18 C22 1.356(4) . ?
N18 C19 1.474(4) . ?
N18 C8 1.480(4) . ?
C1 C7 1.528(4) . ?
C1 C2 1.533(4) . ?
C1 C6 1.542(4) . ?
C1 C8 1.560(4) . ?
C2 C3 1.506(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.511(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.511(4) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.539(4) . ?
C8 H8 1.0000 . ?
C11 C12 1.504(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.377(5) . ?
C12 C17 1.390(5) . ?
C13 C14 1.383(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.372(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.489(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.266(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C22 C23 1.501(4) . ?
C23 C28 1.380(4) . ?
C23 C24 1.383(4) . ?
C24 C25 1.376(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.380(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N10 C11 123.0(3) . . ?
C9 N10 H10 118.7(19) . . ?
C11 N10 H10 117.4(19) . . ?
C22 N18 C19 120.8(2) . . ?
C22 N18 C8 117.7(3) . . ?
C19 N18 C8 120.5(2) . . ?
C7 C1 C2 109.4(2) . . ?
C7 C1 C6 108.9(2) . . ?
C2 C1 C6 109.3(3) . . ?
C7 C1 C8 112.0(3) . . ?
C2 C1 C8 109.5(2) . . ?
C6 C1 C8 107.7(2) . . ?
F2 C2 C3 108.4(3) . . ?
F2 C2 C1 109.5(2) . . ?
C3 C2 C1 112.7(2) . . ?
F2 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
F3 C3 C2 108.8(2) . . ?
F3 C3 C4 108.4(3) . . ?
C2 C3 C4 113.6(2) . . ?
F3 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C3 C4 C5 108.4(3) . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
F5 C5 C4 109.0(2) . . ?
F5 C5 C6 107.9(2) . . ?
C4 C5 C6 111.5(3) . . ?
F5 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
F6 C6 C5 106.3(2) . . ?
F6 C6 C1 110.4(2) . . ?
C5 C6 C1 111.6(2) . . ?
F6 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
C1 C6 H6 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N18 C8 C9 110.1(2) . . ?
N18 C8 C1 112.0(2) . . ?
C9 C8 C1 114.2(2) . . ?
N18 C8 H8 106.7 . . ?
C9 C8 H8 106.7 . . ?
C1 C8 H8 106.7 . . ?
O9 C9 N10 124.0(3) . . ?
O9 C9 C8 122.9(3) . . ?
N10 C9 C8 113.1(3) . . ?
N10 C11 C12 111.7(2) . . ?
N10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C17 118.4(3) . . ?
C13 C12 C11 121.8(3) . . ?
C17 C12 C11 119.6(3) . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
N18 C19 C20 113.8(3) . . ?
N18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
N18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 125.9(4) . . ?
C21 C20 H20 117.0 . . ?
C19 C20 H20 117.0 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
O22 C22 N18 122.6(3) . . ?
O22 C22 C23 118.3(3) . . ?
N18 C22 C23 118.9(3) . . ?
C28 C23 C24 119.8(3) . . ?
C28 C23 C22 119.4(3) . . ?
C24 C23 C22 120.2(3) . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.4(3) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 119.7(3) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C23 C28 C27 120.3(3) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C1 C2 F2 -171.0(2) . . . . ?
C6 C1 C2 F2 69.9(3) . . . . ?
C8 C1 C2 F2 -47.9(3) . . . . ?
C7 C1 C2 C3 68.3(3) . . . . ?
C6 C1 C2 C3 -50.8(3) . . . . ?
C8 C1 C2 C3 -168.6(3) . . . . ?
F2 C2 C3 F3 53.5(3) . . . . ?
C1 C2 C3 F3 174.8(2) . . . . ?
F2 C2 C3 C4 -67.3(3) . . . . ?
C1 C2 C3 C4 54.0(4) . . . . ?
F3 C3 C4 C5 -177.2(2) . . . . ?
C2 C3 C4 C5 -56.1(3) . . . . ?
C3 C4 C5 F5 177.5(2) . . . . ?
C3 C4 C5 C6 58.5(3) . . . . ?
F5 C5 C6 F6 -58.7(3) . . . . ?
C4 C5 C6 F6 60.9(3) . . . . ?
F5 C5 C6 C1 -179.1(2) . . . . ?
C4 C5 C6 C1 -59.5(3) . . . . ?
C7 C1 C6 F6 176.3(2) . . . . ?
C2 C1 C6 F6 -64.2(3) . . . . ?
C8 C1 C6 F6 54.7(3) . . . . ?
C7 C1 C6 C5 -65.6(3) . . . . ?
C2 C1 C6 C5 53.8(3) . . . . ?
C8 C1 C6 C5 172.7(2) . . . . ?
C22 N18 C8 C9 130.6(3) . . . . ?
C19 N18 C8 C9 -37.7(3) . . . . ?
C22 N18 C8 C1 -101.2(3) . . . . ?
C19 N18 C8 C1 90.6(3) . . . . ?
C7 C1 C8 N18 -49.7(3) . . . . ?
C2 C1 C8 N18 -171.2(2) . . . . ?
C6 C1 C8 N18 70.0(3) . . . . ?
C7 C1 C8 C9 76.3(3) . . . . ?
C2 C1 C8 C9 -45.2(4) . . . . ?
C6 C1 C8 C9 -164.0(3) . . . . ?
C11 N10 C9 O9 -4.5(5) . . . . ?
C11 N10 C9 C8 177.4(3) . . . . ?
N18 C8 C9 O9 92.2(3) . . . . ?
C1 C8 C9 O9 -34.9(4) . . . . ?
N18 C8 C9 N10 -89.6(3) . . . . ?
C1 C8 C9 N10 143.3(3) . . . . ?
C9 N10 C11 C12 -96.8(3) . . . . ?
N10 C11 C12 C13 105.4(3) . . . . ?
N10 C11 C12 C17 -70.4(4) . . . . ?
C17 C12 C13 C14 1.7(5) . . . . ?
C11 C12 C13 C14 -174.1(3) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 -1.3(6) . . . . ?
C14 C15 C16 C17 0.8(7) . . . . ?
C15 C16 C17 C12 1.0(7) . . . . ?
C13 C12 C17 C16 -2.2(5) . . . . ?
C11 C12 C17 C16 173.8(4) . . . . ?
C22 N18 C19 C20 -67.8(4) . . . . ?
C8 N18 C19 C20 100.1(3) . . . . ?
N18 C19 C20 C21 123.0(4) . . . . ?
C19 N18 C22 O22 166.0(3) . . . . ?
C8 N18 C22 O22 -2.2(4) . . . . ?
C19 N18 C22 C23 -18.7(4) . . . . ?
C8 N18 C22 C23 173.1(2) . . . . ?
O22 C22 C23 C28 104.9(3) . . . . ?
N18 C22 C23 C28 -70.6(4) . . . . ?
O22 C22 C23 C24 -66.6(4) . . . . ?
N18 C22 C23 C24 117.9(3) . . . . ?
C28 C23 C24 C25 0.0(5) . . . . ?
C22 C23 C24 C25 171.4(3) . . . . ?
C23 C24 C25 C26 -1.1(5) . . . . ?
C24 C25 C26 C27 1.5(5) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C24 C23 C28 C27 0.8(5) . . . . ?
C22 C23 C28 C27 -170.8(3) . . . . ?
C26 C27 C28 C23 -0.4(5) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_32
_database_code_depnum_ccdc_archive 'CCDC 1436761'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_audit_creation_date             2015-09-14
_audit_creation_method           'by CrystalStructure 4.1'


_chemical_formula_sum            'C25 H28 F4 N2 O3'
_chemical_formula_moiety         'C25 H28 F4 N2 O3'
_chemical_formula_weight         480.50
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.768(3)
_cell_length_b                   10.296(3)
_cell_length_c                   22.978(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2310.9(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1999
_cell_measurement_theta_min      25.00
_cell_measurement_theta_max      75.10
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008.00
_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.589
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            7007
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_theta_max         68.327
_diffrn_reflns_theta_min         3.848
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.898
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3780
_reflns_number_gt                3121
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2044
_refine_ls_wR_factor_gt          0.1943
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     312
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1596P)²+2.9344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.07
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(15)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.1738(4) 0.2275(3) 0.80361(17) 0.0480(10) Uani 1 1 d . . . . .
F3 F -0.0712(4) 0.1508(4) 0.8386(2) 0.0586(12) Uani 1 1 d . . . . .
F5 F 0.2468(4) -0.1978(3) 0.85330(14) 0.0424(9) Uani 1 1 d . . . . .
F6 F 0.3652(3) 0.0145(3) 0.81402(14) 0.0345(8) Uani 1 1 d . . . . .
O9 O 0.1604(4) 0.2635(4) 0.65452(19) 0.0377(10) Uani 1 1 d . . . . .
O19 O 0.5856(4) 0.1672(4) 0.74970(17) 0.0344(9) Uani 1 1 d . . . . .
O24 O 0.3755(13) -0.1606(5) 0.4672(2) 0.129(4) Uani 1 1 d . . . . .
N10 N 0.3718(4) 0.3486(4) 0.66774(19) 0.0244(10) Uani 1 1 d D . . . .
N18 N 0.4408(5) 0.0696(4) 0.6858(2) 0.0273(10) Uani 1 1 d . . . . .
C1 C 0.2089(6) 0.0513(6) 0.7351(2) 0.0297(12) Uani 1 1 d . . . . .
C2 C 0.1044(6) 0.1374(6) 0.7685(3) 0.0363(14) Uani 1 1 d . . . . .
H2 H 0.0475 0.1858 0.7396 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0102(6) 0.0613(6) 0.8083(3) 0.0413(15) Uani 1 1 d . . . . .
H3 H -0.0507 0.0055 0.7838 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0860(6) -0.0241(6) 0.8506(3) 0.0362(14) Uani 1 1 d . . . . .
H4A H 0.0206 -0.0727 0.8752 0.043 Uiso 1 1 calc R U . . .
H4B H 0.1453 0.0292 0.8761 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1720(6) -0.1173(6) 0.8149(3) 0.0338(13) Uani 1 1 d . . . . .
H5 H 0.1105 -0.1724 0.7904 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2725(6) -0.0493(5) 0.7767(2) 0.0280(12) Uani 1 1 d . . . . .
H6 H 0.3235 -0.1154 0.7533 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1277(7) -0.0224(7) 0.6878(3) 0.0463(17) Uani 1 1 d . . . . .
H7A H 0.0398 -0.0511 0.7038 0.056 Uiso 1 1 calc R U . . .
H7B H 0.1803 -0.0982 0.6750 0.056 Uiso 1 1 calc R U . . .
H7C H 0.1114 0.0353 0.6546 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3246(5) 0.1410(5) 0.7122(2) 0.0247(11) Uani 1 1 d . . . . .
H8 H 0.3638 0.1824 0.7479 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2770(5) 0.2542(5) 0.6748(2) 0.0249(11) Uani 1 1 d . . . . .
C11 C 0.3484(6) 0.4611(5) 0.6300(2) 0.0273(12) Uani 1 1 d . . . . .
H11A H 0.4088 0.5332 0.6424 0.033 Uiso 1 1 calc R U . . .
H11B H 0.2524 0.4903 0.6343 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3759(5) 0.4299(5) 0.5670(2) 0.0225(11) Uani 1 1 d . . . . .
C13 C 0.2702(6) 0.3947(5) 0.5298(2) 0.0288(12) Uani 1 1 d . . . . .
H13 H 0.1786 0.3956 0.5436 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2964(6) 0.3585(6) 0.4730(3) 0.0346(13) Uani 1 1 d . . . . .
H14 H 0.2229 0.3344 0.4482 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4295(6) 0.3570(6) 0.4520(2) 0.0326(13) Uani 1 1 d . . . . .
H15 H 0.4476 0.3314 0.4131 0.039 Uiso 1 1 calc R U . . .
C16 C 0.5350(6) 0.3932(6) 0.4883(3) 0.0347(14) Uani 1 1 d . . . . .
H16 H 0.6264 0.3934 0.4742 0.042 Uiso 1 1 calc R U . . .
C17 C 0.5089(6) 0.4294(6) 0.5454(3) 0.0309(13) Uani 1 1 d . . . . .
H17 H 0.5827 0.4541 0.5699 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5692(6) 0.0905(5) 0.7096(2) 0.0286(12) Uani 1 1 d . . . . .
C20 C 0.6851(7) 0.0135(7) 0.6839(3) 0.0458(16) Uani 1 1 d . . . . .
H20A H 0.6502 -0.0417 0.6525 0.055 Uiso 1 1 calc R U . . .
H20B H 0.7542 0.0730 0.6683 0.055 Uiso 1 1 calc R U . . .
H20C H 0.7265 -0.0409 0.7141 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4260(6) 0.0043(6) 0.6304(3) 0.0327(13) Uani 1 1 d . . . . .
C22 C 0.4219(10) -0.1286(6) 0.6258(3) 0.061(2) Uani 1 1 d . . . . .
H22 H 0.4330 -0.1806 0.6596 0.073 Uiso 1 1 calc R U . . .
C23 C 0.4013(14) -0.1880(7) 0.5717(3) 0.091(4) Uani 1 1 d . . . . .
H23 H 0.3946 -0.2799 0.5692 0.109 Uiso 1 1 calc R U . . .
C24 C 0.3906(12) -0.1138(8) 0.5221(3) 0.074(3) Uani 1 1 d . . . . .
C25 C 0.4021(7) 0.0185(6) 0.5264(3) 0.0366(15) Uani 1 1 d . . . . .
H25 H 0.3989 0.0698 0.4921 0.044 Uiso 1 1 calc R U . . .
C26 C 0.4180(6) 0.0782(5) 0.5794(2) 0.0283(12) Uani 1 1 d . . . . .
H26 H 0.4237 0.1702 0.5814 0.034 Uiso 1 1 calc R U . . .
C27 C 0.3602(17) -0.2969(18) 0.4597(7) 0.139(5) Uani 1 1 d . U . . .
H27A H 0.3504 -0.3166 0.4182 0.167 Uiso 1 1 calc R U . . .
H27B H 0.4411 -0.3414 0.4751 0.167 Uiso 1 1 calc R U . . .
H27C H 0.2785 -0.3265 0.4806 0.167 Uiso 1 1 calc R U . . .
H10 H 0.464(3) 0.327(6) 0.682(2) 0.028(15) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.404(7) . ?
F3 C3 1.403(8) . ?
F5 C5 1.413(6) . ?
F6 C6 1.410(6) . ?
O9 C9 1.234(7) . ?
O19 C19 1.224(7) . ?
O24 C24 1.358(9) . ?
O24 C27 1.422(19) . ?
N10 C9 1.352(7) . ?
N10 C11 1.465(7) . ?
N10 H10 0.979(7) . ?
N18 C19 1.386(8) . ?
N18 C21 1.447(7) . ?
N18 C8 1.483(7) . ?
C1 C6 1.540(7) . ?
C1 C7 1.546(8) . ?
C1 C8 1.551(8) . ?
C1 C2 1.554(8) . ?
C2 C3 1.515(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.505(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.492(8) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.521(8) . ?
C8 H8 1.0000 . ?
C11 C12 1.507(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.388(7) . ?
C12 C17 1.391(8) . ?
C13 C14 1.380(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(8) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C19 C20 1.503(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.373(9) . ?
C21 C26 1.398(8) . ?
C22 C23 1.400(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(10) . ?
C25 C26 1.372(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O24 C27 118.3(8) . . ?
C9 N10 C11 122.2(4) . . ?
C9 N10 H10 115(4) . . ?
C11 N10 H10 121(4) . . ?
C19 N18 C21 120.7(5) . . ?
C19 N18 C8 117.0(4) . . ?
C21 N18 C8 121.0(4) . . ?
C6 C1 C7 108.2(5) . . ?
C6 C1 C8 108.5(4) . . ?
C7 C1 C8 115.3(5) . . ?
C6 C1 C2 110.1(5) . . ?
C7 C1 C2 106.9(5) . . ?
C8 C1 C2 107.8(4) . . ?
F2 C2 C3 106.8(5) . . ?
F2 C2 C1 110.1(4) . . ?
C3 C2 C1 113.7(5) . . ?
F2 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
F3 C3 C2 107.7(5) . . ?
F3 C3 C4 110.0(6) . . ?
C2 C3 C4 113.1(5) . . ?
F3 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
C3 C4 C5 107.1(5) . . ?
C3 C4 H4A 110.3 . . ?
C5 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
C5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
F5 C5 C6 107.6(5) . . ?
F5 C5 C4 108.7(5) . . ?
C6 C5 C4 112.7(5) . . ?
F5 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
F6 C6 C5 106.5(4) . . ?
F6 C6 C1 108.8(4) . . ?
C5 C6 C1 114.5(5) . . ?
F6 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
C1 C6 H6 109.0 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N18 C8 C9 112.4(4) . . ?
N18 C8 C1 113.7(4) . . ?
C9 C8 C1 115.2(4) . . ?
N18 C8 H8 104.7 . . ?
C9 C8 H8 104.7 . . ?
C1 C8 H8 104.7 . . ?
O9 C9 N10 122.1(5) . . ?
O9 C9 C8 123.7(5) . . ?
N10 C9 C8 114.2(4) . . ?
N10 C11 C12 111.9(4) . . ?
N10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C17 118.3(5) . . ?
C13 C12 C11 121.0(5) . . ?
C17 C12 C11 120.7(5) . . ?
C12 C13 C14 121.0(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.5(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.7(5) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
O19 C19 N18 121.0(5) . . ?
O19 C19 C20 122.6(5) . . ?
N18 C19 C20 116.4(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.5(6) . . ?
C22 C21 N18 122.2(5) . . ?
C26 C21 N18 119.3(5) . . ?
C21 C22 C23 120.5(6) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.3(6) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
O24 C24 C23 125.5(7) . . ?
O24 C24 C25 115.4(6) . . ?
C23 C24 C25 119.1(7) . . ?
C26 C25 C24 121.2(6) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C21 120.4(5) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
O24 C27 H27A 109.5 . . ?
O24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 75.3(6) . . . . ?
C7 C1 C2 F2 -167.4(5) . . . . ?
C8 C1 C2 F2 -42.9(6) . . . . ?
C6 C1 C2 C3 -44.4(6) . . . . ?
C7 C1 C2 C3 72.9(6) . . . . ?
C8 C1 C2 C3 -162.6(5) . . . . ?
F2 C2 C3 F3 54.2(6) . . . . ?
C1 C2 C3 F3 175.7(5) . . . . ?
F2 C2 C3 C4 -67.6(7) . . . . ?
C1 C2 C3 C4 54.0(7) . . . . ?
F3 C3 C4 C5 -179.7(5) . . . . ?
C2 C3 C4 C5 -59.2(7) . . . . ?
C3 C4 C5 F5 179.0(4) . . . . ?
C3 C4 C5 C6 59.8(6) . . . . ?
F5 C5 C6 F6 -55.1(5) . . . . ?
C4 C5 C6 F6 64.8(6) . . . . ?
F5 C5 C6 C1 -175.4(4) . . . . ?
C4 C5 C6 C1 -55.5(6) . . . . ?
C7 C1 C6 F6 170.2(5) . . . . ?
C8 C1 C6 F6 44.4(6) . . . . ?
C2 C1 C6 F6 -73.4(5) . . . . ?
C7 C1 C6 C5 -70.8(6) . . . . ?
C8 C1 C6 C5 163.4(5) . . . . ?
C2 C1 C6 C5 45.6(6) . . . . ?
C19 N18 C8 C9 104.6(5) . . . . ?
C21 N18 C8 C9 -62.3(6) . . . . ?
C19 N18 C8 C1 -122.2(5) . . . . ?
C21 N18 C8 C1 70.9(6) . . . . ?
C6 C1 C8 N18 53.6(6) . . . . ?
C7 C1 C8 N18 -68.0(6) . . . . ?
C2 C1 C8 N18 172.8(4) . . . . ?
C6 C1 C8 C9 -174.6(4) . . . . ?
C7 C1 C8 C9 63.9(6) . . . . ?
C2 C1 C8 C9 -55.4(6) . . . . ?
C11 N10 C9 O9 -7.2(8) . . . . ?
C11 N10 C9 C8 175.8(4) . . . . ?
N18 C8 C9 O9 119.4(6) . . . . ?
C1 C8 C9 O9 -13.0(7) . . . . ?
N18 C8 C9 N10 -63.7(6) . . . . ?
C1 C8 C9 N10 163.9(5) . . . . ?
C9 N10 C11 C12 -81.7(6) . . . . ?
N10 C11 C12 C13 96.0(6) . . . . ?
N10 C11 C12 C17 -80.8(6) . . . . ?
C17 C12 C13 C14 0.9(8) . . . . ?
C11 C12 C13 C14 -176.0(5) . . . . ?
C12 C13 C14 C15 -0.2(9) . . . . ?
C13 C14 C15 C16 -0.5(9) . . . . ?
C14 C15 C16 C17 0.7(9) . . . . ?
C15 C16 C17 C12 0.0(9) . . . . ?
C13 C12 C17 C16 -0.7(8) . . . . ?
C11 C12 C17 C16 176.1(5) . . . . ?
C21 N18 C19 O19 165.0(5) . . . . ?
C8 N18 C19 O19 -1.9(7) . . . . ?
C21 N18 C19 C20 -15.4(7) . . . . ?
C8 N18 C19 C20 177.7(5) . . . . ?
C19 N18 C21 C22 85.3(9) . . . . ?
C8 N18 C21 C22 -108.3(8) . . . . ?
C19 N18 C21 C26 -93.6(7) . . . . ?
C8 N18 C21 C26 72.8(7) . . . . ?
C26 C21 C22 C23 -4.0(15) . . . . ?
N18 C21 C22 C23 177.1(9) . . . . ?
C21 C22 C23 C24 2.7(19) . . . . ?
C27 O24 C24 C23 4(2) . . . . ?
C27 O24 C24 C25 -178.7(13) . . . . ?
C22 C23 C24 O24 177.5(12) . . . . ?
C22 C23 C24 C25 0.8(19) . . . . ?
O24 C24 C25 C26 -179.9(9) . . . . ?
C23 C24 C25 C26 -2.8(16) . . . . ?
C24 C25 C26 C21 1.4(12) . . . . ?
C22 C21 C26 C25 2.0(10) . . . . ?
N18 C21 C26 C25 -179.1(6) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
